BR112014001057B1 - 2,3-DIPHENYLVALERONITRILE DERIVATIVES, PROCESSES FOR THE PREPARATION AND USE OF VEGETABLE HERBICIDES AND REGULATORS - Google Patents

Abstract

Patent Summary for: "2,3-diphenylvaleronitrile derivatives, processes for their preparation and their use as herbicides and plant growth regulators". The invention relates to compounds of formula (I) wherein l is a radical of formula (a), and a1, b1 and a2 and b2 have the meanings defined in claim 1 which are suitable as herbicides for the invention. control of harmful plants or as plant growth regulators. The compounds may be prepared by the process according to claim 12. 1/1

Description

(54) Title: 2,3-DIFENYLVALERONITRYL DERIVATIVES, PROCESSES FOR THEIR PREPARATION AND USE AS HERBICIDES AND REGULATORS OF VEGETABLE GROWTH (51) Int.CI .: C07D 231/12; C07D 231/16; C07D 231/20; C07D 261/08; C07D 319/06; C07C 255/62; C07C 255/66; C07C 325/02 (30) Unionist Priority: 7/15/2011 FROM 10 2011 079 241.4, 7/15/2011 US 61 / 508,306 (73) Holder (s): BAYER INTELLECTUAL PROPERTY GMBH (72) Inventor (s): MARC MOSRIN; HARALD JAKOBI; ALFRED ANGERMANN; ELMAR GATZWEILER; ISOLDE HÀUSER-HAHN; INES HEINEMANN; CHRISTOPHER HUGH ROSINGER; STEFAN LEHR; STEFAN SCHNATTERER

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Invention Patent Descriptive Report for: 2,3 DIPHENYLVALERONITRYL DERIVATIVES, PROCESSES FOR THEIR PREPARATION AND USE WHILE HERBICIDES AND REGULATORS OF VEGETABLE GROWTH.

[001] The invention concerns the technical field of herbicides and plant growth regulators, for example, herbicides for the control of broadleaf herbs and weeds, optionally in useful plant cultures, or plant growth regulators which can be used to influence the growth of crop plants.

[002] In terms of their application, crop protection agents known to date for the selective control of harmful plants in useful plant cultures or active compounds for the control of unwanted vegetation sometimes have such disadvantages such as (a) showing no herbicidal activity or showing insufficient herbicidal activity against particular harmful plants, (b) the spectrum of harmful plants that can be controlled with an active compound is not sufficiently broad, (c) their selectivity in crops of useful plants are too small and / or (d) have an unfavorable profile from a toxicological point of view. In addition, some active compounds that can be used as plant growth regulators for various useful plants cause undesired reduced crop yields in other useful plants or are either not compatible with the crop plant or are compatible only at a reduced application rate. Some of the known active compounds cannot be produced on an industrial scale from an economic point of view due to the fact that precursors and reagents are difficult to obtain or have insufficient chemical stability. In the case of other active compounds, the activity is highly dependent on environmental conditions, such as climate and soil conditions.

[003] The cianobutiratos herbicides are described in patent applications unpublished EP-A-5341, EP-A-266 725 (US 4,224,052),

2/289

EP-A-270830, JP-04/297454, JP-04/297455, JP-05/058979, WO 2011/003775, WO 2011/003776, WO 2011/042378 and WO 2011/073143.

[004] EP-A-5341 describes herbicidal esters and amides of 4-cyano-3,4-diphenylbutanoic acids which are optionally substituted in the phenyl radicals. According to EP-A-5341, treo isomers are normally suitable for non-selective control of harmful plants, whereas mixtures of erythro / treo isomers are suitable for selective control of harmful plants in some plant cultures Useful. In addition, document EP-A-5341 states that the 2 enantiomers that belong to the treus form have different activities, which was investigated in an exemplary way on the different activities of the enantiomers of the 4-cyano-3 acid enantiomers, 4-diphenylbutanoic unsubstituted in phenyl radicals.

[005] EP-A-266725 describes some mixtures of erythro / threo isomers that can be used selectively for the control of weeds in rice crops.

[006] In document EP-A-270830 it is described that threo isomers and mixtures of erythro / threo isomers can be used as plant regulators, preventing the development of an infrutescence in several harmful weeds.

[007] WO 2011/003775 describes specific esters of 4-cyano-3,4-diphenylbutanoic acids which can be used as effective herbicides, also preferably in useful plant cultures.

[008] WO 2011/003776, WO 2011/042378 and WO 2011/073143 describe 4-cyano-3,4-diphenylbutanoic esters and acids which have specific substitutions in the phenyl radicals and which can be used as effective herbicides , also preferably in useful plant cultures.

[009] The herbicidal activity of compounds known to the class of substances

3/289 mentioned, in particular for reduced application rates, and / or their compatibility with crop plants continue to require development. [010] For the reasons mentioned, there is still a need for alternative herbicides with high activity for selective application in crop plants or use in non-cultivated land. It is also desirable to provide alternative chemically active compounds that can be advantageously used as herbicides or as plant regulators.

[011] Therefore, it is an object of the present invention to provide compounds that have herbicidal activity, which are quite effective against harmful economically important plants, even for reduced application rates, and which can be used selectively in crop plants, preferably with good activity against harmful plants.

[012] Surprisingly, it has now been found that compounds with an additional structural modification in the acid or ester group compared to the active compounds of the mentioned cyanobutyrates and which belong to the group of 2,3-diphenylvaleronitrile derivatives have a herbicidal action special and, in some cultures, can preferably be used for the selective control of harmful plants.

[013] The present invention provides compounds of formula (I), or their salts,

whereas the symbol L represents a radical of structural formula A ¹ A ² or the symbol A ¹ represents oxygen, sulfur or = NR ^A ,

4/289 the symbol B ¹ represents a radical of structural formulas (B1) to (B14), O

R

R

Q (B5)

O

R

R (B7) (B8), 8

Q

R

R

R, 12 (B6)

O

^ ^X R · '(B9), 29

R

Q

R

27 ^ O

5/289

R

O

R ° 'Q (B14) the symbol A ² represents a radical of structural formula (A1) to (A12),

R

-R

R w

R ¹⁹

R ²⁰ (A7)

(A2)

O

R (A8)

R

R

(A9)

6/289

O

(A10) (A11) (A12) the symbol B ² represents hydroxy, uncle, halogen or a group of general formula OR ³³ , OM, SR ³⁴ , SM or -NRBRC, each of the symbols W ¹ and W ⁶ represents, in independently of each other, the divalent oxygen, sulfur group or a group of the general formula NH, N [C1-4 alkyl], C = O (carbonyl), S = O (sulfinyl), SO2 (sulfonyl) or CR ³⁵ R ³⁶ , each of the symbols W ² , W ³ , W ⁴ , W ⁵ and W ⁷ independently represents the divalent oxygen, sulfur group or a group of the general formula NH, N- [alkyl (Ci-C4)], C = O (carbonyl), S = O (sulfinyl) or SO2 (sulfonyl), each of the symbols Q ¹ , Q ² , Q ³ , Q ⁴ , Q ⁵ , Q ⁶ , Q ⁷ , Q ⁸ and Q ⁹ represent. Independently of each other, hydroxy, uncle, halogen or a group of general formula OR ³⁷ , SR ³⁸ , SM or OM, the symbol M represents an equivalent of a cation, preferably an equivalent of a metal ion, an ion of ammonium which is optionally substituted with 1 to 4 radicals, the same or different, selected from the group consisting of alkyl (C-C6), alkenyl (C2-C6), alkynyl (C2-C6), cycloalkyl (C3-C6), cycloalkenyl (C5-C6), cycloalkynyl (C5-C6), phenyl, cycloalkyl (C3-C6) -alkyl (C1-C4), cycloalkenyl (C5-C6) -alkyl (C-C4), phenyl20 alkyl (C1-C4) or a tertiary sulfonium ion that is preferably substituted with 3 radicals, the same or different, selected from the group consisting of alkyl (C-C6), alkenyl (C2-C6), alkynyl (C2-C6), cycloalkyl (C3-C6) , cycloalkenyl (C5-C6), cycloalkynyl (C5-C6), phenyl, cycloalkyl (C3-C6) -alkyl (C1-C4), cycloalkenyl (C5-C6) -alkyl (C1-C4), phenyl-alkyl (Ci -C4) and, in particular, (C25 C4) alkyl,

7/289 each of the symbols R ^A , R ^B and R ^C independently represents hydrogen, hydroxy, alkoxy (C-C4), alkyl (C-C4), haloalkyl (C-C4), phenyl or benzyl, wherein each of the two radicals referred to last is optionally mono- or poly-substituted with the same or different substituents and, preferably and independently of one another, unsubstituted or substituted with one or more radicals selected from the set consisting of halogen, alkyl (C4), haloalkyl (C1-C4), alkoxy (C1-C4) and haloalkoxy (C1-C4), or -NR * R **, where each of the symbols R *, R ** independently represents H, alkyl (C1-Ce), alkenyl (C2-C8), alkynyl (C2-Ce), alkoxy (C1-C4) -alkyl (C1-C4), alkanoyl ( C1-C6) [haloalkyl (C1-C4)] - carbonyl, [alkoxy (C1-C4)] - carbonyl, [haloalkoxy (C1-C4)] - carbonyl, cycloalkyl (C3-C6), cycloalkyl (C3-C6) -alkyl (C1-C4), phenyl, phenyl-alkyl (C1-C4), where each of these last 4 radicals is unsubstituted in the cycle or is sub substituted with one or more radicals selected from the group consisting of halogen, alkyl (Ci C4), haloalkyl (Ci-C4), alkoxy (Ci-C4) and haloalkoxy (Ci-C4) or, in the case of cycloalkyl, also oxo or the symbols R * and R **, together with the nitrogen atom, represent a 3- to 8-membered heterocycle, which, in addition to the nitrogen atom, may contain one or two other ring hetero atoms selected from the set consisting of N, O and S, which can be unsubstituted or substituted with one or more radicals selected from the group consisting of alkyl (C1-C4), haloalkyl (C1-C4) and oxo, the symbol (R ⁱ ) m represents m substituents R ⁱ , where R ⁱ , if m = 1, or each of the substituents R ⁱ , if m is greater than 1, independently represents halogen, cyano, nitro, hydroxy, alkyl ( C1-C), alkenyl (C2-C6), alkynyl (C2-C6), alkoxy (C1-C), alkyl (C1-C8) -thio, alkyl (C1-C8) -sulfinyl, alkyl (C1-C8) -sulfonyl , haloalkyl (C1-C6), haloalkoxy (C1-C6), halo (C1-C6) -thio, haloalkyl (C1-C6) -sulfinyl, haloalkyl (C1-C6) -sulfonyl, haloalkenyl (C2-C6), haloalkynyl (C2-C6), alkoxy (C-C6) ) -alkyl (C1-4), haloalkoxy (C1-C6) -alkyl (C1-C4), cycloalkyl (C3-C6) which is optionally

8/289 substituted with one or more radicals selected from the group consisting of halogen and alkyl (Ci-C4), cycloalkoxy (C3-C6) which is optionally substituted with one or more radicals selected from the group consisting of halogen and alkyl (Ci -C4), or a radical of the general formula C (O) OR ³⁹ , C (O) NR ⁴⁰ R ⁴¹ , C (O) -Het ¹ , NR ⁴² R ⁴³ or Het ² or where each of the two groups R ¹ located in the ortho position on the ring together represent a group of the general formula -Z ¹ -A * -Z ² , in which the symbol A * represents an alkylene group having between 1 and 4 carbon atoms and which is optionally substituted with one or more radicals selected from the group consisting of halogen, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1-C4) and haloalkoxy (C1-C4), the symbol Z ¹ represents a direct bond , O or S and the symbol Z ² represents a direct bond, O or S, in which the group -Z ¹ -A * -Z ² , together with the carbon atoms attached to the group, of phenyl ring forms a condensed ring with 5 or 6 members and the symbol (R ² ) n represents n substituents R ² , where the substituent R ² , if n = 1, or each of the substituents R ² , if the symbol n is greater than 1, independently represents halogen, cyano, nitro, hydroxy, alkyl (C1-Ce), alkenyl (C2-C6), alkynyl (C2-C6), alkoxy (C1-C8), alkyl (C1-Ce) -thio, (C1-Ce) -sulfinyl, (C1-Ce) -sulfonyl, halo (C1-C6), haloalkoxy (C1-C6), haloalkyl (C1-C6) -io, haloalkyl (C1-C6) -sulfinyl, haloalkyl (C1C6) -sulfonyl, haloalkenyl (C2-C6), haloalkynyl (C2-C6), alkoxy (C1-C6) -alkyl (C1C4), haloalkoxy (C1-C6) -alkyl ( C1-C4), cycloalkyl (C3-C6) which is optionally substituted with one or more radicals selected from the group consisting of halogen and alkyl (C1-C4), cycloalkoxy (C3-C6) which is optionally substituted with one or more radicals selected from the group consisting of halogen and alkyl (C1-C4), or the radical of general formula C (O) OR ⁴⁴ , C (O) NR ⁴⁵ R ⁴⁶ , C (O) -Het ³ , NR ⁴⁷ R ⁴⁸ or Het ⁴ or where two R ² groups located in an ortho position on the ring, together,

9/289 represent a group of the general formula -Z ³ -A ** - Z ⁴ , in which the symbol A ** represents an alkylene group having between 1 and 4 carbon atoms and which is optionally substituted with one or more radicals selected from the group consisting of halogen, alkyl (Ci-C4), haloalkyl (Ci-C4), alkoxy (Ci-C4) and haloalkoxy (Ci-C4), the symbol Z ³ represents a direct bond, O or S and the symbol Z ⁴ represents a direct bond, O or S, in which the group -Z ³ -A ** - Z ⁴ , together with the carbon atoms attached to the group, of the phenyl ring form a condensed ring with 5 or 6 members , each of the symbols R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ independently represent hydrogen, halogen, cyano, nitro, hydroxy, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1-C4), haloalkoxy ( C1-C4), alkoxy (C1-C4) -alkyl (C1-C4), haloalkoxy (C1-C4) -alkyl (C1-C4), cycloalkyl (C3-C6), hal ocycloalkyl (C3-C6), cycloalkoxy (C3-C6), alkenyl (C2-C6), haloalkenyl (C2-C6), alkynyl (C2-C6), haloalkynyl (C2-C6), alkyl (C1-C4) -io , (C1-C4) alkylsulfonyl, (C1-C4) alkylsulfinyl, phenyl which is optionally substituted and preferably unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, (C1-C4) alkyl, haloalkyl (C1-C4), alkoxy (C1-C4) and haloalkoxy (C1-C4) or a C (O) group OR ⁴⁹ , C (O) NR ⁵⁰ R ⁵¹ , C (O) Het ⁵ , NR ⁵² R ⁵³ or Het ⁶ or the symbols R ³ and R ⁵ , in the group of formula (B1) or (A1), together represent a divalent bridge of a straight chain alkylene or alkenylene group having 2 or 3 carbon atoms, where a CH2 group in the chain can also be replaced by an oxygen atom and where a CH2 group or a CH group in the chain is optionally substituted with one or more radicals selected from the group consisting of (C1-C4) alkyl, haloalkyl (C1-C4), alkoxy (C1-C4) and haloalkoxy (C1-C4), preferably a divalent aliphatic tip of general formula -CH2CH2-, -CH2CH2CH2-, -CH (CH3) CH2-, C (CH3) 2CH2-, -CH2CH (CH3) -, -CH2C ( CH3) 2-, -C (CH3) CH (CH3) -, -CH2CH2CH2-, -CH = CH-, -CH = CHCH2-, -CH2CH = CH-, -OCH2-, -CH2O-, -OCH2CH2-, 10/289

CH2OCH2-, -CH2CH2O- or -OCH2O- and, in particular, of the general formula -CH2CH2or -CH = CH-, the symbol R ²¹ represents hydrogen, alkyl (C 1 -C ₄ ), haloalkyl (C 1 -C ₄ ), cycloalkyl (C3-C6), halocycloalkyl (C3-C6) or a group C (O) OR ⁵⁴ , C (O) NR ⁵⁵ R ⁵⁶ , C (O) Het ⁷ , NR ⁵⁷ R ⁵⁸ or Het ⁸ , the symbol R ²² represents hydrogen, (C1-C4) alkyl, halo (C1-C4), cycloalkyl (C3-C6), halocycloalkyl (C3-C6), alkyl (C1-C4) -thio, alkyl (C1-C4) sulfonyl, alkyl ( C1-C4) -sulfinyl or a group of general formula C (O) OR ⁵⁹ , C (O) NR ⁶⁰ R ^ei , C (O) Het ⁹ , NR ⁶² R ⁶³ or Het ⁱ⁰ , each of the symbols R ²³ and R ²⁹ independently represents hydrogen, alkyl (C1-C4), haloalkyl (C1-C4), cycloalkyl (C3-C6), halocycloalkyl (C3-C6), alkoxy (C1-C4) or haloalkoxy ( C-C4), each of the symbols R ²⁴ and R ³⁰ independently represents hydrogen, halogen, cyano, alkyl (C-C4), haloalkyl (C-C4), cycloalkyl (C3C6), halocycloalkyl ( C3-C6), alkoxy (C1-C4) or haloalkoxy (C1-C4), ca one of the symbols R ²⁵ , R ²⁶ , R ³ⁱ and R ³² independently represents hydrogen, alkyl (C 1 -C 4), haloalkyl (C 1 -C 4), alkoxy (C 1 -C 4), haloalkoxy (Ci -C4), alkoxy (C1-C4) -alkyl (C1-C4), haloalkoxy (C1-C4) -alkyl (C1-C4), cycloalkyl (C3-C6), halocycloalkyl (C3-C6), cycloalkoxy (C3- C6), alkenyl (C2-C6), haloalkenyl (C2-C6), alkynyl (C2-C6), haloalkynyl (C2-C6), alkyl (C1-C4) -thio, alkyl (C1-C4) -sulfonyl, alkyl (C1-C4) -sulfinyl, NR ⁶⁴ R ⁶⁵ or Het ⁱⁱ , the symbol R ²⁷ represents hydrogen, (C1-C6) alkyl, haloalkyl (C1-C4), cycloalkyl (C3-C6) or halocycloalkyl (C3-C6) , the symbol R ²⁸ represents hydrogen, (C 1 -C 6) alkyl, haloalkyl (C 1 C) or a radical of the general formula C (O) OR ⁶⁶ , each of the symbols R ³³ , R ³⁴ , R ³⁷ and R ³⁸ represents , independently of one another, alkyl (C-C8), cycloalkyl (C3-C6), phenyl, in which each of these last three radicals, independently of each other, is unsubstituted or substituted with one or more radicals selected between and the set consisting of halogen, cyano, nitro, hydroxy, (C1-C4) alkoxy, (C1-C4) alkyl, and, in the case of

11/289 a cycloalkyl radical or phenyl as the original radical, also alkyl (C 1 -C 4) and haloalkyl (C 1 -C 4), or a group of general formula -C (O) R ⁶⁷ , -C (O) OR ⁶⁸ , C (O) NR ⁶⁹ R ⁷⁰ , -C (O) Het ¹² or -SO2R ⁷¹ , each of the symbols R ³⁵ and R ³⁶ , independently of each other, has the meaning defined for the symbol R ³ or, preferably , represents hydrogen, (C1 -C4) alkyl or haloalkyl (C1-C4), each of the symbols R ³⁹ , R ⁴⁴ , R ⁴⁹ , R ⁵⁴ , R ⁵⁹ and R ⁶⁶ independently represents hydrogen, alkyl (C-C4), haloalkyl (C-C4), cycloalkyl (C3-C6), halocycloalkyl (C3-C6), alkenyl (C2-C4), haloalkenyl (C2-C4), alkynyl (C2-C4) or said group M and preferably (C 1 -C 4) alkyl, each of the symbols R ⁴⁰ , R ^{4 1} , R ⁴² , R ⁴³ , R ⁴⁵ , R ⁴⁶ , R ⁴⁷ , R ⁴⁸ , R ⁵⁰ , R ^{5 1} , R ⁵² , R ⁵³ , R ⁵⁵ , R ⁵⁶ , R ⁵⁷ , R ⁵⁸ , R ⁶⁰ , R ^{6 1} , R ⁶² , R ⁶³ , R ⁶⁴ , R ⁶⁵ , R ⁶⁹ and R ⁷⁰ represent, independently between si, hydrogen, (C-C6) alkyl, alkenyl (C2-C6) or alkynyl (C2C6), where each of these last 3 radicals, independently of each other, is unsubstituted or is substituted with one or more radicals selected from the group consisting of halogen, nitro, cyano and phenyl, which is optionally substituted and is preferably unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, nitro, cyano, alkyl (C1-C4) and haloalkyl (C1-C4), or cycloalkyl (C3-C6) or phenyl, in that each of these last 2 radicals, independently of each other, is unsubstituted or is substituted with one or more radicals selected from the group consisting of halogen, nitro, cyano, alkyl (Ci-C4), haloalkyl (Ci-C4 ), phenyl or benzyl, where each of these last 2 radicals is optionally substituted and is preferably unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, nitro, cyano, (C-C4) alkyl and haloalkyl (CiC4), the symbol R ⁶⁷ represents hydrogen, alkyl (Ci-C8) or haloalkyl (Ci-C8), in which each of these last 2 radicals, independently of each other, is optionally interrupted in the alkyl residue by oxygen or sulfur, or

12/289 represents phenyl or benzyl, in which each of these last 2 radicals, independently of each other, is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, cyano, alkyl (C1-C4 ), alkenyl (C2-C4), alkynyl (C2-C4), cycloalkyl (C3-C6), haloalkyl (C-C4) and halocycloalkyl (C3-C6), the symbol R ⁶⁸ represents alkyl (Ci-Ce), haloalkyl (C1-C8), cycloalkyl (C3-C6), halocycloalkyl (C3-C6), alkenyl (C2-C8), haloalkenyl (C2-C8) or alkynyl (C2-C4), the symbol R ⁷¹ represents alkyl (C1- C6), haloalkyl (C1-C6) or phenyl or benzyl, in which each of these last 2 radicals, independently of each other, is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, cyano , (C-C4) alkyl, alkenyl (C2-C4), alkynyl (C2-C4), cycloalkyl (C3-C6), haloalkyl (C-C4) and halocycloalkyl (C3-C6), each of the symbols Het ⁱ , Het ² , Het ³ , Het ⁴ , Het ⁵ , Het ⁶ , Het ⁷ , Het ⁸ , Het ⁹ , Het ⁱ⁰ , Het ⁱ ' ¹ and Het ⁱ² independently represent a saturated or partially unsaturated radical of a heterocycle that have between 3 and 9 atoms in the ring and at at least one nitrogen atom as the ring hetero atom at position 1 of the ring and optionally 1, 2 or 3 other ring hetero atoms selected from the group consisting of N, O and S, where the radical of the heterocycle is linked by the nitrogen atom at position 1 of the ring to the remainder of the molecule of the compound of structural formula (I) and in which the heterocycle is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, (C-C4) alkyl, haloalkyl ( (C1-C4), (C1-C4) alkoxy, (C1-C4) haloalkoxy, (C1-C4) alkylthio and oxo, and preferably represents the saturated heterocycle radical of the type referred to, in particular a group morpholino, piperidine or pyrrolidine and each of the men symbols represents , independently of each other, 0, 1,2, 3, 4 or 5 and preferably 0, 1,2 or 3.

[014] In structural formula (I), the general formula (R1) m designates m radicals R1 which are attached as substituents on the phenyl ring in question, where the radicals in case the symbol m is greater than 1 can be the same or different and

13/289 have the meaning mentioned in each case in more detail. In the case of m = 0, then the phenyl ring in question is unsubstituted with R ¹ substituents, that is, all the carbon atoms in the phenyl ring at positions 2 to 6 are attached to a hydrogen atom. Correspondingly, this also applies to the replacement of the other phenyl ring according to general formula (R ² ) n.

[015] In the structural formulas (B1) to (B14) for the radicals of the group B1, the free bond through which the group B1 in the group of general formula -C (= A1) -B1 is attached to the carbon atom shown in formula is represented by an arrow (**), to avoid that it is confused with an abbreviated notification for the radical “methyl”.

[016] In structural formulas (A1) to (A12) for group A ² radicals, the free double bond through which group A ² in the group of formula -C (= A ² ) -B ² is attached to the atom of carbon presented in the formula is represented by an arrow (^ ==), to prevent it from being confused with an abbreviated notification for the radical “methylene” (H2C =).

[017] The compounds of structural formula (I) according to the invention comprise all stereoisomers, which may occur based on centers of asymmetry or double bonds in the molecule, whose configuration is not specifically designated in the formula or which are not explicitly specified , and mixtures thereof, including racemic compounds and mixtures partially enriched with particular stereoisomers. The invention also comprises all tautomers, such as keto and enol tautomers, and mixtures and salts thereof, if suitable functional groups are present. [018] In positions 2 and 3 of the main structure of substituted valeronitrile, the compounds of formula (I) contain two chirality centers, so they occur in at least four stereoisomers and their mixtures, that is, 2 enantiomeric and 2 erythro isomers treo enantiomeric isomers. Depending on the substituents (R ¹ ) m and (R ² ) n, one or more different chirality centers may be present.

14/289 [019] Therefore, the invention also provides erythro / threus mixtures (diastereomeric mixtures) of the compounds of formula (I).

[020] The invention also provides the erythro racemic isomers or the treo racemic isomers of the compounds of formula (I).

[021] The invention also provides the optically active erythro (2R, 3S) and (2S, 3R) isomers and mixtures thereof that have an excess of one enantiomer (see following structural formula (I), where the positions in the main structure of valeronitrile are numbered from 1 to 5).

[022] The invention also provides the optically active (2R, 3R) and (2S, 3S) isomers and mixtures that have an excess of one enantiomer.

[023] Due to the two chirality centers in positions 2 and 3, compounds with the same chemical constitution exist in the form of 4 stereoisomeric configurations, namely two erythro enantiomers that exhibit the configurations (2R, 3S) [= erythro-1] and (2S, 3R) [= erythro-2], respectively, and two treo enantiomers that exhibit the configurations (2S, 3S) [= treo-1] and (2R, 3R) [= treo-2], respectively; see diagram below:

Erythro-1 (2R, 3S)

Erythro-2 (2S, 3R)

15/289

Treo-2 (2R, 3R) [024] The compounds (I) according to the invention represent mixtures of diastereomers of the 4 stereoisomers, but also comprise the diastereomeric forms erythro and treus separately, in each case as a racemic mixture of the enantiomers erythro or the treo enantiomers or as pure or stereochemically enriched enantiomers erythro-1, erythro-2, treo1 or treo-2.

[025] Mixtures of diastereomers of structural formula (I) (erythro / threo mixtures) are preferred.

[026] In addition, racemic mixtures treo of structural formula (I) of the above mentioned enantiomers treo-1 and treo-2 in a 50:50 ratio are preferred.

[027] Even more preferred are the enantiomers (2R, 3R) treo-2 of structural formula (Ia), or their salts,

(Ia)

Treo-2 (2R, 3R) in which the substituents (R ¹ ) m and (R ² ) n have the meaning defined for the structural formula (I), in which the stereochemical configuration on the carbon atom at position 2 of the valeronitrile derivative has a stereochemical purity of 60% to 100% (R), preferably 70% to 100% (R), more preferably 80% to 100% (R) and, in particular, 90% to 100% (R) based on the mixture of

16/289 threus enantiomers present and the stereochemical configuration on the carbon atom at position 3 of the valeronitrile derivative has a stereochemical purity of 60% to 100% of (R), preferably 70% to 100% of (R), more preferably from 80% to 100% of (R) and, in particular, from 90% to 100% of (R), based on the mixture of the treo enantiomers present.

[028] In the case of suitable acidic substituents, the compounds of formula (I) are capable of forming salts, upon reaction with bases, in which the acidic hydrogen is replaced by an agriculturally suitable cation.

[029] By adding an inorganic or organic acid suitable to a basic group, such as, for example, amino or alkylamino, compounds of formula (I) are capable of forming salts. Suitable acidic groups present, such as, for example, carboxylic acid groups, are capable of forming internal salts with groups which, in turn, can be protonated, such as amino groups.

[030] Preferably, the compounds of formula (I) may be present in the form of salts usable from an agricultural point of view, in which the type of salt is otherwise indifferent. In general, suitable salts include salts of those cations or acid addition salts of those acids whose cations and anions, respectively, have no adverse effects on the herbicidal activity of the compounds (I).

[031] In particular, suitable cations include alkali metal ions, preferably lithium, sodium or potassium, alkaline earth metals, preferably calcium or magnesium, and transition metals, preferably manganese, copper, zinc or iron. The cation used for being ammonium or substituted ammonium, in which one to four hydrogen atoms can be replaced by alkyl (C1-C4), hydroxy-alkyl (C1-C4), alkoxy (C1-C4) -alkyl (C1-C4) ), hydroxy (C1-C4) -alkyl (C1-C4), phenyl or benzyl, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2- (217/289 hydroxy-et-1-oxy) -et- 1-yl-ammonium, di- (2-hydroxy-et-1-yl) -ammonium, trimethylbenzylammonium. Phosphonium ions, sulfonium ions, preferably tri-methyl (C1-C4) -sulfonium, or sulfoxonium ions, preferably trimethyl (C1-C4) -sulfoxonium, are also suitable.

[032] Useful anions of acid addition salts mainly refer to chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluoro silicate, hexafluorophosphate, benzoate and also the anions of alkanoic acids (C1-C4), preferably, format, acetate, propionate, butyrate or trifluoroacetate.

[033] In structural formula (I) and in all subsequent structural formulas, chemical radicals are referred to by names that represent collective terms for the enumeration of members of an individual group or else they refer specifically to individual chemical radicals. In general, terms that are familiar to those skilled in the art and / or, in particular, have the meanings illustrated below are used.

[034] A hydrocarbon radical is a monocyclic organic radical or, in the case of an optionally substituted hydrocarbon radical, also bicyclic or polycyclic, aliphatic, cycloaliphatic or aromatic based on the elements carbon and hydrogen, including, for example, the alkyl, alkenyl radicals , alkynyl, cycloalkyl, cycloalkenyl, aryl, phenyl, naphthyl, indanyl, indenyl, etc .; such correspondingly applying to hydrocarbon radicals in compound meanings, such as hydrocarbonoxy radicals or other hydrocarbon radicals linked through groups of heteroatoms.

[035] Except when defined in more detail, hydrocarbon radicals preferably have between 1 and 20 carbon atoms, more preferably between 1 and 16 carbon atoms and, in particular, between 1 and 12 carbon atoms. The hydrocarbon radicals, also in the special alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio radicals, and also in the corresponding unsaturated and / or substituted radicals, can in each case be straight-chain or branched-chain in the main carbon structure.

18/289 [036] The term "(C1-C4) alkyl" represents an abbreviated notation for alkyl that has between 1 and 4 carbon atoms, that is, it comprises the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl. In general, alkyl radicals with a wider specified range of carbon atoms, e.g. (C1 -C6) alkyls, also correspondingly comprise straight or branched chain alkyl radicals with a higher number of carbon atoms, that is, according to the example, also comprise the alkyl radicals with 5 and 6 atoms of carbon.

[037] Unless specifically indicated, lower carbon structures are preferable, for example, having between 1 and 6 carbon atoms or having between 2 and 6 carbon atoms in the case of unsaturated groups, in the case of hydrocarbyl radicals, such as alkyl, alkenyl and alkynyl radicals, including compound radicals. As alkyl radicals, including in combined definitions, such as alkoxy, haloalkyl, etc., refers, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls , hexyls, such as n-hexyl, ihexyl and 1,3-dimethylbutyl, heptylates, such as n-heptyl, 1-methylhexyl and 1,4dimethylpentyl; alkenyl and alkynyl radicals are defined as possible unsaturated radicals that correspond to alkyl radicals; as alkenyl, for example, a vinyl, allyl, 1-methyl-2-propenyl, 2-methyl-2propenyl, 2-butenyl, pentenyl, 2-methylpentenyl or hexenyl group and preferably allyl, 1-methylpropyl -2-ene-1-yl, 2-methylprop-2-ene-1-yl, but-2-ene-1-yl, but-3-ene1-yl, 1-methylbut-3-ene-1-yl or 1-methylbut-2-ene-1-yl.

[038] An alkenyl radical also comprises, in particular, straight or branched chain hydrocarbon radicals that have more than double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also alenyl or cumulenyl radicals that have a or more accumulated double bonds, for example, alenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl.

[039] The alkynyl radical includes, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl.

[040] The alkynyl radical also comprises, in particular, radicals

19/289 straight or branched chain hydrocarbons having more than one triple bond or having one or more triple bonds and one or more double bonds, for example, 1,3-butatrienyl or 3-pentene-1-innocence 1-ila.

[041] The carbocyclic ring with 3 to 9 members refers to cycloalkyl (C3-C9) or cycloalkenyl (C5-C9).

[042] Cycloalkyl (C3-C9) refers to a saturated carbocyclic ring system that preferably has 3 to 9 carbon atoms, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cycloheptyl or cyclononyl. In the case of substituted cycloalkyl, cyclic systems with substituents are included, in which the substituents can also be linked via a double bond to the cycloalkyl radical, for example, an alkylidene group, such as methylidene.

[043] Cycloalkenyl (C5-C9) refers to a partially unsaturated, non-aromatic carbocyclic ring system that has between 5 and 9 carbon atoms, for example, 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2cyclopentenyl, 3-cyclopentenyl or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or 1,4-cyclohexadienyl. In the case of a substituted cycloalkenyl, the meanings for substituted cycloalkyl can be applied accordingly.

[044] The term alkylidene, for example, also in the form of alkylidene (CiCio), designates the radical of a straight or branched chain alkane that is linked through a double bond, the position of the bonding site is not fixed. In the case of a branched alkane, the only possible positions are, of course, those in which two hydrogen atoms can be replaced by the double bond; radicals refer, for example, to = CH ₂ , = CH-CH3, = C (CH3) -CH3, = C (CH3) -C2H5 or = C (C2H5) -C2H5.

[045] The term halogen means, for example, fluorine, chlorine, bromine or iodine. The terms halo-alkyl, halo-alkenyl and haloalkynyl refer to alkyl, alkenyl and alkynyl, respectively, which are partially or completely substituted with the same or different halogen atoms, preferably selected from the group

20/289 consisting of fluorine, chlorine, bromine and iodine, in particular, selected from the group consisting of fluorine, chlorine and bromine and more particularly selected from the group consisting of fluorine and chlorine, for example, monohaloalkyl, perhaloalkyl, CF3 , CHF2, CH2F, CF3CF2, CHzFCHCl, CCb, CHCl2, CHzCHzCl; haloalkoxy represents, for example, OCF3, OCHF2, OCH2F, CF3CF2O, OCH2CF3 and OCH2CH2Cl; correspondingly applying this definition to haloalkenyl and other halogen substituted radicals, such as, for example, halocycloalkyl.

[046] The term aryl represents a mono-, bi- or poly-cyclic aromatic system, for example, phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, where the point of attachment is in the aromatic system.

[047] The optionally substituted aryl group also comprises polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, where the point of attachment is in the aromatic system.

[048] A heterocyclic radical (heterocyclyl) comprises at least one heterocyclic ring (= carbocyclic ring in which at least one carbon atom is replaced by a heteroatom and, preferably, by a heteroatom selected from the group consisting of N, O, S, P, B, Si, Se), which is saturated, unsaturated or heteroaromatic and which can be unsubstituted or substituted, where the point of attachment is located on a ring atom.

[049] Unless otherwise defined, it preferably contains one or more, in particular 1, 2 or 3 hetero atoms in the heterocyclic ring, preferably selected from the group consisting of N, O, and S; it is preferably an aliphatic heterocyclyl radical having 3 to 7 ring atoms or a heteroaromatic radical having 5 or 6 ring atoms. The heterocyclic radical can be, for example, a heteroaromatic radical or a (heteroaryl) ring, such as, for example, a monocyclic, bicyclic or polycyclic aromatic system in which at least 1 ring contains one or more heteroatoms.

[050] If the heterocyclyl radical or the heterocyclic ring is optionally substituted, then it can be fused to other carbocyclic rings or

21/289 heterocyclic. Benzo-fused heterocyclic or heteroaromatic rings are preferred.

[051] An optionally substituted heterocyclyl also comprises polycyclic systems, such as, for example, 8-aza-bicyclo [3.2.1] octanyl or 1aza-bicyclo [2.2.1] heptyla.

[052] An optionally substituted heterocyclyl also comprises spirocyclic systems, such as, for example, 1-oxa-5-aza-spiro [2.3] hexyl. [053] Preferably, it is a radical of a heteroaromatic ring that has a heteroatom of the set consisting of N, O and S, for example, the radical of a ring with five or six members, such as pyridyl, pyrrolyl, thienyl or furyl ; more preferably, it is a radical of a corresponding heteroaromatic ring having 2, 3 or 4 hetero atoms, for example, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, tetrazinyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyazolyl, triazolyl or imidazolyl or tetrazolyl.

[054] In this case, a radical of a five or six membered heteroaromatic ring having between 1 and 4 hetero atoms is preferred, such as, for example,

1.2.3- triazolyl, 1,2,4-triazolyl, tetrazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1, 2,3-thiadiazolyl, 1,2,4 thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, tetrazolyl, 1,2,3-triazinyl, 1,2,4 triazinyl, 1,3,5- triazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5-tetrazinyl, 1,2,4,5-tetrazinyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl.

[055] In this case, heteroaromatic radicals of five-membered heterocycles that have 3 nitrogen atoms, such as

1.2.3- triazol-1-yl, 1,2,3-triazol-4-yl, 1,2,3-triazol-5-yl, 1,2,5-triazol-1-yl, 1,2, 5triazol-3-yl, 1,3,4-triazol-1-yl, 1,3,4-triazol-2-yl, 1,2,4-triazol-3-yl, 1,2,4-triazole ila;

also more preferred, in this case, the heteroaromatic radicals of six-membered heterocycles that have 3 nitrogen atoms, such as

1,3,5-triazine-2-yl, 1,2,4-triazine-3-yl, 1,2,4-triazine-5-yl, 1,2,4-triazine-6-yl,

1.2.3-triazine-4-yl, 1,2,3-triazine-5-yl;

22/289 are also more preferred, in this case, the heteroaromatic radicals of five-membered heterocycles having two nitrogen atoms and one oxygen atom, such as 1,2,4-oxadiazole-3-yl; 1,2,4-oxadiazol-5-yl, 1,3,4oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2, 5-oxadiazol-3-yl, are also more preferred, in this case, heteroaromatic radicals of five-membered heterocycles that have two nitrogen atoms and a sulfur atom, such as 1,2,4-thiadiazole-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4 thiadiazol-2-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2, 5-thiadiazol-3-yl; more preferred, in this case, are the heteroaromatic radicals of five-membered heterocycles that have four nitrogen atoms, such as 1,2,3,4-tetrazol-1-yl, 1,2,3,4-tetrazol-5 -yl, 1,2,3,5-tetrazol-1-yl, 1,2,3,5tetrazol-4-yl, 2H-1,2,3,4-tetrazol-5-yl, 1H-1,2 , 3,4-tetrazol-5-yl, are also more preferred, in this case, the heteroaromatic radicals of six-membered heterocycles, such as 1,2,4,5-tetrazine-3-yl; more preferred in this case are heteroaromatic radicals of five-membered heterocycles having three nitrogen atoms and one oxygen or sulfur atom, such as 1,2,3,4-oxatriazole-5-yl; 1,2,3,5oxatriazol-4-yl; 1,2,3,4-thiatriazole-5-yl; 1,2,3,5-thiatriazole-4-yl; more preferred in this case are the heteroaromatic radicals of six-membered heterocycles, such as, for example, 1,2,4,6-thiatriazine-1-yl; 1,2,4,6-thiatriazine-3-yl; 1,2,4,6-thiatriazine-5-yl.

[056] Even more preferably, the heterocyclic radical or ring is a partially or fully hydrogenated heterocyclic radical that has a hetero atom of the group consisting of N, O and S, for example, oxiranyl, oxetanyl, oxolanyl (= tetrahydrofuryl), oxanyl, pyrrolinyl, pyrrolidyl or piperidyl.

[057] Also preferably it is a partially or fully hydrogenated heterocyclic radical that has two heteroatoms of the set consisting of N, O and S, for example, piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl and morpholinyl. Suitable substituents for a substituted heterocyclic radical include the following substituents

23/289 specified and, in addition, also oxo. The oxo group can also occur in hetero-ring atoms that are capable of existing in different oxidation states, such as, for example, in the case of N and S.

[058] Preferred examples of heterocyclic include a heterocyclic radical having between 3 and 6 atoms in the ring consisting of pyridyl, thienyl, furyl, pyrrolyl, oxiranyl, 2-oxetanyl, 3-oxetanyl, oxolanyl (= tetrahydrofuryl) , pyrrolidyl, piperidyl, in particular, oxiranyl, 2-oxetanyl, 3-oxetanyl or oxolanyl, or a heterocyclic radical having two or three heteroatoms, for example, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thiazolyl, thiadiazolyl, isazole, pyrazolyl, triazolyl, piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl or morpholinyl.

[059] Preferred heterocyclic radicals also include benzo-fused heteroaromatic rings, for example benzofuryl, benzisofuryl, benzothiophenyl, benzisothiophenyl, isobenzothiophenyl, indolyl, isoindolyl, indazolyl, benzimidazolyl, benzotriazolyl, benzotriazolyl, 1,2 1benzisoxazolyl, benzothiazolyl, 1,2-benzisothiazolyl, 2,1-benzisothiazolyl, 1,2,3benzoxadiazolyl, 2,1,3-benzoxadiazolyl, 1,2,3-benzothiadiazolyl, 2,1,3benzothiadiazolyl, quinolyl (quinolinyl), isoquinolyl (isoquinolinyl), quinolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzotriazinyl, purinyl, pteridinyl, indolizinyl, benzo-1,3-dioxylyl, 4H-benzo-1,3-dioxinyl and 4H-benzo1,4-dioxinyl, and, when possible, its N-oxides and salts.

[060] When a base structure is replaced “with one or more radicals” selected from a list of radicals (= group) or a generically defined group of radicals, this comprises, in each case, simultaneous substitution with several structurally identical radicals and / or different.

[061] Substituted radicals, such as alkyl, alkenyl, alkynyl, cycloalkyl, aryl, phenyl, benzyl, heterocyclyl and substituted heteroaryl radicals, are, for example, a substituted radical obtained from an unsubstituted base structure, where the substituents are, for example, one or more and, preferably, 1, 2 or 3 radicals selected from the group consisting of

24/289 halogen, alkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino, such as acylamino, mono- and dialkylamino, and alkylsulfinyl, alkylsulfonyl and, in the case of cyclic radicals, also alkyl, haloalkyl, alkylthioalkyl, alkoxyalkyl, mono- and dialkylaminoalkyl optionally substituted and hydroalkyl; in the term substituted radicals, such as substituted alkyl, etc., the substituents include, in addition to the saturated radicals mentioned, the corresponding unsaturated aliphatic and aromatic radicals, such as alkenyl, alkynyl, alkenyloxy, alkynyloxy, phenyl and phenoxy optionally substituted. In the case of substituted cyclic radicals having aliphatic residues in the ring, cyclic systems with such substituents which are attached to the ring via a double bond are also included, for example, substituted with an alkylidene group, such as methylidene or ethylidene.

[062] The term "radicals selected from the group consisting of (followed by the group = list of substituents)" is intended to be synonymous with the term "radicals selected from the group consisting of (...)". The expression "one or more radicals selected from the group consisting of (followed by the group = list of substituents)" is intended to be synonymous with the expression "one or more radicals the same or different selected from the group consisting of (...)". [063] The substituents presented by way of example (“first level of substituents”) can be, if they include fractions containing hydrocarbons ”, themselves substituted if desired (“ second level of substituents ”), for example, with one of the substituents , as defined for the first level of substituents. Correspondingly, other levels of substituents are possible. Preferably, the term "substituted radical" comprises only one or two levels of substituents.

[064] The term "original radical" refers to the respective base structure of a radical to which the substituents of a level of substituents are attached.

[065] As preferred substituents for the levels of substituents refers,

25/289 for example, amino, hydroxyl, halogen, nitro, cyano, mercapto, carboxyl, carbonamide, SF5, aminosulfonyl, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, monoalkylamino, dialkylamino, N-alkanoylamino, alkoxy, alkyleneyl, alkoxy, alkyleneyl cycloalkoxy, cycloalkenyloxy, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, aryloxycarbonyl, alkanoyl, alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl, alkylthio, cycloalkylthio, alkenyl, cycloalkenyl, alkylalkyl, alkylalkyl, sulfonyl, alkylalkyl, sulfonyl, alkylen dialkylaminocarbonyl, N-alkanoylaminocarbonyl, N-alkanoyl-N-alkylamino-carbonyl, aryl, aryloxy, benzyl, benzylaxy, benzylthio, arylthio, arylamino and benzylamino.

[066] Two substituents together can also form a bridge of saturated or unsaturated hydrocarbons or a corresponding point at which carbon atoms, CH groups or CH2 groups are replaced by hetero atoms, thus forming a fused or fused cycle. In this case, systems fused with benzene are preferably formed based on the base structure.

[067] An optionally substituted phenyl group is preferably a phenyl or phenyl that is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, cyano, alkyl (C1-C4), haloalkyl (C1-C4 ), (C1-C4) alkoxy - (C1-C4) alkyl, (C1-C4) alkoxy, (C1-C4) haloalkoxy, (C1-C4) alkoxy (C1-C4) alkoxy, (C1-C4) alkyl -thio and nitro, and, in particular, phenyl which is optionally substituted with one or more radicals selected from the group consisting of halogen, alkyl (C-C4), haloalkyl (C-C4) and alkoxy (CiC4).

[068] In the case of radicals having carbon atoms, those having between 1 and 6 carbon atoms, preferably between 1 and 4 carbon atoms and, in particular, 1 or 2 carbon atoms are preferred. In general, substituents from the group consisting of halogen, e.g., fluorine and chlorine, alkyl (C1-C4), preferably methyl or ethyl, haloalkyl (C1-C4), are preferred.

26/289 preferably trifluoromethyl, C1-4 alkoxy, preferably methoxy or ethoxy, haloalkoxy (C1-4), nitro and cyano. In this case, methyl, methoxy, fluorine and chlorine substituents are particularly preferred.

[069] A substituted amino, such as mono- or di-substituted amino, designates a radical in the group consisting of substituted amino radicals that are N substituted, for example, with one or two identical or different radicals selected from the group consisting of alkyl, alkoxy, acyl and aryl; preferably mono- and di-alkylamino, mono- and di-arylamino, acylamino, N-alkyl-Narylamino, N-alkyl-N-acylamino and N-heterocycles; alkyl radicals having between 1 and 4 carbon atoms are preferred; aryl is preferably phenyl or substituted phenyl; acyl is as defined below, preferably (C 1 -C 4) alkanoyl. The same also applies to hydroxylamino or substituted hydrazino.

[070] Acyl is a radical of an organic acid that is formed, in the formal sense, by removing a hydroxyl group in the acid function and the organic radical in the acid can also be linked to the acid function through a heteroatom. Examples of acyl include the radical -CO-R of a HO-CO-R carboxylic acid and acid radicals derived therefrom, such as those of thiocarboxylic acid, optionally N-substituted iminocarboxylic acids or the carbon monoester radical, acid N-substituted carbamic acid, sulfonic acids, sulfinic acids, N-substituted sulfonamide acids, phosphonic acids or phosphonic acids.

[071] Acyl is, for example, formyl, alkylcarbonyl, such as [(C1 -C4 alkyl)] carbonyl, phenylcarbonyl, alkyloxycarbonyl, phenyloxycarbonyl, benzylaxicarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl and other radicals of organic acids . Each of the radicals can also be substituted in the alkyl or phenyl residue, for example, in the alkyl residue with one or more radicals selected from the group consisting of halogen, alkoxy, phenyl and phenoxy; examples of substituents on the phenyl residue include those mentioned above in general terms for substituted phenyl.

27/289 [072] Preferably, the term acyl means an acyl radical in the narrowest sense, that is, a radical of an organic acid in which the acid group is directly linked to the carbon atom of an organic radical, for example, formyl, alkylcarbonyl, such as acetyl or [(C1 -C4 alkyl)] - carbonyl, phenylcarbonyl, alkylsulfonyl, alkylsulfinyl and other organic acid radicals.

[073] More preferably, the term acyl designates an alkanoyl radical having between 1 and 6 carbon atoms and, in particular, between 1 and 4 carbon atoms. In this case, the term alkanoyl (C1-C4) designates an alkanoic acid radical that has between 1 and 4 carbon atoms formed after removal of the OH group from the acid group, that is, formyl, acetyl, n-propionyl, isopropionyl or n-, i-, sec- or tert-butanoyl.

[074] The "ilo position" of a radical means the carbon atom that has the free bond.

[075] The compounds of formula (I) according to the invention and the compounds of formula (I) used according to the invention and / or their salts are referred to in short for "compounds (I)".

[076] The invention also provides all stereoisomers that are covered by structural formula (I) and mixtures thereof. Such compounds of structural formula (I) contain one or more asymmetric carbon atoms or else double bonds that are not referred to separately in the structural formulas (I). The possible stereoisomers defined by their specific three-dimensional structure, such as enantiomers, diastereomers, Z and E isomers, are all covered by structural formula (I) and can be obtained from mixtures of the stereoisomers by conventional methods or else they can be prepared by means of of stereoselective reactions in conjunction with the use of stereochemically pure starting materials.

[077] The invention also provides all the tautomers of compounds of formula (I) that can be obtained from the displacement of a hydrogen atom (for example, keto-enol tautomers). The compound of structural formula (I) also comprises tautomers, even though,

28/289 formally, structural formula (I) correctly describes only one of the respective tautomers that are in equilibrium with the other or that can be converted into the other. For example, compounds of formula (I), where L represents a radical of formula (L '), where L represents a radical of general formula -C (= A ¹ ) -B ¹ , the symbol A ¹ represents an oxygen atom and the symbol B ¹ represents a radical of structural formula (B1) in which the symbol Q ¹ represents OH, are tautomers of the compounds of structural formula (I), in which the symbol L represents a radical of structural formula (L ''), where the symbol L corresponds to a radical of general formula -C (= A ² ) -B ² , the symbol A ² represents a radical of structural formula (A1) and the symbol B ² represents an OH group (see diagram):

R ⁴

(L '') [078] Thus, the tautomers of compounds (I) with (L ') and (L'') are both within the scope of structural formula (I), where the symbol L represents a radical of formula general -C (= A ¹ ) -B ¹ and by the scope of structural formula (I), where the symbol L represents a radical of general formula -C (= A ² ) -B ² .

[079] The compounds of structural formula (I) also comprise all physical forms in which they can be present as a pure substance or, if appropriate, as a mixture with other compounds, in particular, also in polymorphic crystal forms of the compounds of structural formula (I) and its salts and solvates (for example, hydrates).

[080] Mainly for reasons of superior herbicidal activity, better selectivity, better yield, better formulation capacity and / or other relevant properties, the compounds of the structural formula (I) mentioned before according to the invention, or their salts, are particularly interesting

29/289 or its use according to the invention, wherein the individual radicals have one of the meanings already specified or specified below or, in particular, where one or more of the preferred meanings already specified or specified below occur in combination.

[081] The compounds of formula (I) according to the invention and their uses according to the invention with the following preferred meanings of the chemical symbols or radicals or chemical groups in question are particularly interesting, regardless of the other respective radicals according to the symbols (R ¹ ) m and (R ² ) n, L and the definitions of the men symbols in the structural formula (I) and the definitions of the radicals (or chemical groups) according to the symbols A ¹ , A ² , B ¹ , B ² , R ^A , R ^B , W ¹ to W ⁷ , Q ¹ to Q ⁹ , M, R ³ to R ⁷¹ , R * and R ** in the corresponding under-meanings of the radicals in the structural formula (I ).

[082] Compounds (I) in which the symbol (R ¹ ) m represents m substituents R ¹ are preferred, where the substituent R ¹ , if m = 1, or each of the substituents R ¹ , if m is greater than 1, independently represents halogen, cyano, nitro, hydroxy, alkyl (C1-Ce), alkenyl (C2-C4), alkynyl (C2-C4), alkoxy (C1-C6), alkyl (C1 -Ce) -thio, (C1-Ce) alkylsulfinyl, (C1-C6) alkylsulfonyl, halo (C1-C4) haloalkyl (C1-C4), haloalkyl (C1-C4) -io, haloalkyl (C1 -C4) -sulfinyl, haloalkyl (C1C4) -sulfonyl, haloalkenyl (C2-C4), haloalkynyl (C2-C4), alkoxy (C1-C4) -alkyl (C1C4), haloalkoxy (C1-C4) -alkyl (C1- C4), cycloalkyl (C3-C6) which is optionally substituted with one or more radicals selected from the group consisting of halogen and alkyl (C1-C4), cyclolalkoxy (C3-C6) which is optionally substituted with one or more radicals selected from among the set consisting of halogen and (C1-C4) alkyl, or a radical of the general formula C (O) OR ³⁹ , C (O) NR ⁴⁰ R ⁴¹ , C ( O) -Het ¹ , NR ⁴² R ⁴³ or Het ² or where, in each case, two R ¹ groups located in an ortho position on the ring, together, form a group of general formula -Z ¹ -A * -Z ² , in which the symbol A * represents an alkylene group having between 1 and 4 atoms of

30/289 carbon and which is optionally substituted with one or more radicals selected from the group consisting of halogen, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1-C4) and haloalkoxy (C1-C4), the symbol Z ¹ represents a direct bond, O or S and the symbol Z ² represents a direct bond, O or S, where the group -Z ¹ -A * -Z ² , together with the carbon atoms, attached to the group of the phenyl ring, form a fused 5- or 6-membered ring, the symbol R ³⁹ represents hydrogen, alkyl (C-C4), haloalkyl (C-C4), cycloalkyl (C3-C6), halocycloalkyl (C3-C6), alkenyl (C2-C4), haloalkenyl (C2-C4), alkynyl (C2-C4) or the mentioned M group and preferably hydrogen, alkyl (C-C4) or the mentioned M group, the symbols R ⁴⁰ , R ^{4 1} , R ⁴² , R ⁴³ , Het ⁱ and Het ² have the meanings mentioned, preferably each of the symbols R ⁴⁰ , R ⁴ⁱ , R ⁴² and R ⁴³ represents, independently of each other, hydrogen or alkyl ( Ci-C4) that is unsubstituted or is replaced with a or more radicals selected from the group consisting of halogen, nitro, cyano and phenyl, or cycloalkyl (C3-C6) or phenyl, in which each of these last 2 radicals, in each case and independently of the others, is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, alkyl (C1-C4), haloalkyl (C1-C4), phenyl or benzyl and, in particular, hydrogen, alkyl (C1-C4) or haloalkyl (C1-4) C4), each of the symbols Het ⁱ and Het ² independently represents a saturated or partially unsaturated radical of a heterocycle that has 3 to 6 ring atoms and at least one nitrogen nitrogen as ring hetero atoms in the position 1 of the ring and, optionally, 1, 2 or 3 other hetero atoms in the ring of the set consisting of N, O and S, where the radical of the heterocycle is connected through the nitrogen atom in position 1 of the ring to the remaining part of the molecule of the compound of structural formula (I) and in which the heterocycle is unsubstituted or is substituted with one or more radicals

31/289 selected from the group consisting of halogen, alkyl (C-C4), haloalkyl (C-C4) and oxo and preferably represents the radical of a saturated heterocycle of the type mentioned, in particular, a morpholino, piperidine group or pyrrolidine, and m represents 0, 1,2, 3, 4 or 5 and preferably 0, 1, 2 or 3.

[083] Compounds (I) are more preferred, where the symbol (R ¹ ) m represents m substituents R ¹ , where the substituent R ¹ , if m = 1, or each of the substituents R ¹ , if m is greater than 1, independently represents halogen, cyano, nitro, hydroxy, (C1-C4) alkyl, (C1-C4) alkoxy, (C1-C4) alkyl, thio (C1-C4) alkyl sulfinyl, (C1-C4) alkylsulfonyl, halo (C1-C4) haloalkoxy (C1-C4), haloalkyl (C1-C4) -thio, haloalkyl (C1-C4) -sulfinyl, haloalkyl (C1-C4) - sulfonyl, alkoxy (C1-C4) -alkyl (C1-C4), cycloalkyl (C3-C6) or a radical of the general formula C (O) OR ³⁹ , C (O) NR ⁴⁰ R ⁴¹ , C (O) -Het ¹ , NR ⁴² R ⁴³ or Het ² , or in which, in each case, two R ¹ groups, located in an ortho position on the ring, together, constitute a group of general formula -Z ¹ -A * -Z ² , in whereas the symbol A * represents an alkylene group having between 1 and 4 carbon atoms and which is optionally substituted with one or more radicals selected from the group consisting of halogen, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1-C4) and haloalkoxy (C1-C4), the symbol Z ¹ represents a direct bond, O or S and the symbol Z ² represents a direct bond, O or S, where the -Z ¹ -A * -Z ^{2 group} , together with the carbon atoms attached to the phenyl ring group, form a fused 5- or 6-membered ring, the symbol R ³⁹ represents hydrogen, alkyl (C1-C4) or the mentioned M group, each of the symbols R ⁴⁰ , R ⁴¹ , R ⁴² and R ⁴³ independently represents hydrogen, (C1-C4) alkyl, haloalkyl (C1-C4) , benzyl, cycloalkyl (C3C6) or phenyl and, in particular, hydrogen, methyl or ethyl, each of the symbols Het ¹ and Het ² independently represents a morpholino, piperidine or pyrrolidine group and

32/289 the symbol m represents 0, 1,2, 3, 4 or 5 and preferably 0, 1, 2 or 3.

[084] Here, compounds (I) are more preferred, where the symbol (R ¹ ) m represents m substituents R ¹ , where the substituent R ¹ , if m = 1, or each of the substituents R ¹ , if m is greater than 1, independently represents halogen, cyano, nitro, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, (C1-C2) alkylsulfinyl, (C1C2) alkylsulfonyl, haloalkyl (C1-C2), haloalkoxy (C1-C2), haloalkyl (C1-C2) -thio, haloalkyl (C1-C2) -sulfinyl, haloalkyl (C1-C2) -sulfonyl or alkoxy (C1-C2) -alkyl (C1C2 ), in particular, each of the R ¹ substituents independently represents halogen, such as fluorine, chlorine, bromine or iodine, or cyano, nitro, methyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl, trifluoromethyl, trifluoromethoxy , trifluoroalkylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl and, in particular, halogen, such as fluorine, chlorine or bromine, and the symbol m represents 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2, 3 or 4 and , in particular 0, 1, 2 or 3.

[085] Even more preferred are compounds of formula (I), or their salts, in which the symbol m is 0 (= the number zero, that is, no R ¹ substituents are present, that is, all free bonds in the ring are occupied by hydrogen) or, preferably, the symbol (R ¹ ) m represents 2-bromine, 3-bromine, 4-bromine, 2-chlorine, 3-chlorine, 4-chlorine,

2- fluorine, 3-fluorine, 4-fluorine, 2-cyano, 3-cyano, 4-cyano, 2-methyl, 3-methyl, 4-methyl, 2-ethyl, 3-ethyl, 4-ethyl, 2-CF3, 3-CF3, 4-CF3, 2-methoxy, 3-methoxy, 4-methoxy, 2-ethoxy,

3-ethoxy, 4-ethoxy, 2-methylthio, 3-methylthio, 4-methylthio, 2-methylsulfinyl, 3-methylsulfinyl, 4-methylsulfinyl, 2-methylsulfonyl, 3-methylsulfonyl, 4-methylsulfonyl, 2-nitro, 3-nitro, 4nitro, 2,3-dimethyl, 2,4-dimethyl, 2,5-dimethyl, 2,6-dimethyl, 3,4-dimethyl, 3,5-dimethyl, 2,3-difluor, 2,4-difluor, 2, 5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro, 2,3dichloro, 2,4-dichloro, 2,5-dichloro, 2,6-dichloro, 3,4-dichloro, 3,5-dichloro, (2-Cl-3-F), (233/289

CI-4-F), (2-CI-5-F), (2-CI-6-F), (3-CI-2-F), (3-CI-4-F), (3- CI-5-F), (3-CI-6-F), (4-CI2-F), (4-CI-3-F), 2,3,4-trifluor, 2,3,5-trifluor , 2,3,6-trifluor, 2,4,6-trifluor, 3,4,5trifluor, 2,3,4-trichlor, 2,3,5-trichlor, 2,3,6-trichlor, 2,4 , 6-tricIoro, 3,4,5-tricIoro or (4-Br-3-F), (3-Br-4-F), (3-Br-5-F), (4-Br-3 -CI), (3-Br-4-CI), (4-CN-3-F), (3CN-4-F), (3-CN-5-F), (4-CN-3-CI ) or (3-CN-4-CI), where the numbering of the radicals refers to the position of the radical in the pheniI-1-iIa radical where the carbon atom attached to position 2 of the main structure of valeronitrile has position 1 in the ring.

[086] The compounds of formula (I), or their salts, are much more preferred, in which the symbol (R ¹ ) m represents 3-bromo, 4-bromo, 3-chloro, 4-chloro, 3-fluoro, 4-fluorine, 2-cyano, 3-cyan, 4-cyan, 2,5-difluor, 3,4-difluor, 3,5-difluor, 3,4-dichloro, 3,5-dichloro, (3-CI-4 -F), (3-CI-5-F), (4-CI-3-F), (3-Br-4-F), (4-Br-3-F), 3,4,5- trifluor, 3,4,5trichlor or (4-Br-3-F), (3-Br-4-F), (3-Br-5-F), (4-Br-3-CI), ( 3-Br-4-CI), (4CN-3-F), (3-CN-4-F), (3-CN-5-F), (4-CN-3-CI) or (3- CN-4-CI).

[087] In this case, the following are particularly preferred:

compounds of formula (I), or their salts, wherein (R ¹ ) m represents 3-chloro;

compounds of formula (I), or their salts, wherein (R ¹ ) m represents 4-chloro;

compounds of the structural formula (I), or their salts, in which the symbol (R ¹ ) m represents 3-fluorine;

compounds of structural formula (I), or their salts, in which the symbol (R ¹ ) m represents 4-fluorine;

compounds of the structural formula (I), or their salts, wherein the symbol (R ¹ ) m represents 3-cyano;

compounds of structural formula (I), or their salts, in which the symbol (R ¹ ) m represents (3-CN-4-F);

compounds of the structural form (I), or their salts, in which the symbol (R ¹ ) m represents (3-Br-4-F);

34/289 compounds of formula (I), or their salts, in which the symbol (R ¹ ) m represents 3,4-difluoro;

compounds of formula (I), or their salts, wherein (R ¹ ) m represents 3,4-dichloro;

compounds of formula (I), or their salts, wherein (R ¹ ) m represents 3,5-difluoro;

compounds of formula (I), or their salts, wherein (R ¹ ) m represents 3,5-dichloro;

compounds of formula (I), or their salts, wherein (R ¹ ) m represents (3-Cl-4-F);

compounds of formula (I), or their salts, wherein (R ¹ ) m represents (3-Cl-5-F);

compounds of formula (I), or their salts, in which the symbol (R ¹ ) m represents (4-Cl-3-F).

[088] Compounds (I) are also preferred, where the symbol (R ² ) n represents n substituents R ² , where the substituent R ² , if n = 1, or each of the substituents R ² , in the case of n is greater than 1, independently represents halogen, cyano, nitro, hydroxy, alkyl (C-C6), alkenyl (C2-C4), alkynyl (C2-C4), alkoxy (C-C6) , (C1-C) alkylthio, (C1-C6) alkylsulfinyl, (C1-C6) alkylsulfonyl, halo (C1-C4) haloalkyl (C1-C4), haloalkyl (C1-C4) -io , halo (C1-C4) -sulfinyl, haloalkyl (C1-C4) -sulfonyl, haloalkenyl (C2-C4), haloalkynyl (C2-C4), alkoxy (C1-C4) -alkyl (C1-C4), haloalkoxy (C1-C4) - alkyl (C1-C4), cycloalkyl (C3-C6) which is optionally substituted with one or more radicals selected from the group consisting of halogen and alkyl (C-C4), cyclolalkoxy (C3-C6) which is optionally substituted with one or more radicals selected from the group consisting of halogen and alkyl (C1-C4), or a radical of general formula C ( O) OR ⁴⁴ , C (O) NR ⁴⁵ R ⁴⁶ , C (O) -Het ³ , NR ⁴⁷ R ⁴⁸ or Het ⁴ or where, in each case, two R ² groups, located in an ortho position on the ring, in together constitute a group of general formula -Z ³ -A ** - Z ⁴ , where

35/289 the symbol A ** represents an alkylene group that has between 1 and 4 carbon atoms and that is optionally substituted with one or more radicals selected from the group consisting of halogen, alkyl (C-C4), haloalkyl (Ci- C4), alkoxy (Ci-C4) and haloalkoxy (Ci-C4), the symbol Z ³ represents a direct bond, O or S and the symbol Z ⁴ represents a direct bond, O or S, where the group -Z ³ -A ** - Z ⁴ , together with the carbon atoms attached to the phenyl ring group, form a fused 5- or 6-membered ring, the symbol R ⁴⁴ represents hydrogen, (C-C4) alkyl, haloalkyl (C- C4), cycloalkyl (C3-C6), halocycloalkyl (C3-C6), alkenyl (C2-C4), haloalkenyl (C2-C4), alkynyl (C2-C4) or the mentioned M group, the symbols R ⁴⁵ , R ⁴⁶ , R ⁴⁷ , R ⁴⁸ , Het ³ and Het ⁴ have the meanings mentioned, preferably each of the symbols R ⁴⁵ , R ⁴⁶ , R ⁴⁷ and R ⁴⁸ represents, independently of each other, hydrogen or alkyl (Ci- C4) that is unsubstituted or substituted c om one or more radicals selected from the group consisting of halogen, nitro, cyano and phenyl, or cycloalkyl (C3-C6) or phenyl, in which each of these last 2 radicals, in each case and independently of the other, is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, alkyl (C-C4), haloalkyl (C-C4), phenyl or benzyl, each of the symbols Het ³ and Het ⁴ represents, in a different way independent of each other, a saturated or partially unsaturated radical of a heterocycle that has between 3 and 6 ring atoms and at least one nitrogen atom as the ring heteroatom at position 1 of the ring and, optionally, 1, 2 or 3 other hetero atoms in the ring ring of the set consisting of N, O and S, in which the radical of the heterocycle is attached through the nitrogen atom at position 1 of the ring to the remaining part of the molecule of the compound of formula (I) and in which the heterocycle is unsubstituted or is replaced with one or more ra dicals selected from the group consisting of halogen, (C1-C4) alkyl,

36/289 haloalkyl (C 1 -C 4) and oxo, and preferably represents the radical of a saturated heterocycle of the type mentioned, in particular a morpholino, piperidine or pyrrolidine group, and n represents 0, 1, 2, 3 , 4 or 5 and preferably 0, 1, 2 or 3.

[089] In this case, compounds (I) are more preferred, where the symbol (R ² ) n represents n substituents R ² , where the substituent R ² , if n = 1, or each of the substituents R ² , if n is greater than 1, it independently represents halogen, cyano, nitro, hydroxy, (C1-C4) alkyl, (C1-C4) alkoxy, (C1-C4) alkyl, thio (Ci -C4) sulfinyl, (C1-C4) alkylsulfonyl, halo (C1-C4) haloalkoxy (C1-C4), haloalkyl (C1-C4) -thio, haloalkyl (C1-C4) -sulfinyl, haloalkyl (Ci- C4) -sulfonyl, (C1-C4) alkoxy (C1-C4), cycloalkyl (C3-C6) or a radical of the general formula C (O) OR ⁴⁴ , C (O) NR ⁴⁵ R ⁴⁶ , C (O ) -Het ³ , NR ⁴⁷ R ⁴⁸ or Het ⁴ , or where, in each case, two R ² groups, located in the ortho position on the ring, together form a group of general formula -Z ³ -A ** - Z ⁴ , in which the symbol A ** represents an alkylene group having between 1 and 4 carbon atoms and which is optionally substituted with one or more radicals selected from the group of halogen, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1-C4) and haloalkoxy (C1-C4), the symbol Z ³ represents a direct bond, O or S and the symbol Z ⁴ represents a direct bond, O or S, where the -Z ³ -A ** - Z ^{4 group} , together with the carbon atoms attached to the phenyl ring group, form a fused 5 or 6 membered ring, the symbol R ⁴⁴ represents hydrogen, (C 1 -C 4) alkyl or the mentioned group M, the symbols R ⁴⁵ , R ⁴⁶ , R ⁴⁷ , R ⁴⁸ , Het ³ and Het ⁴ have the meanings mentioned, preferably each of the symbols R ⁴⁵ , R ⁴⁶ , R ⁴⁷ and R ⁴⁸ independently represent hydrogen, alkyl (C-C4), haloalkyl (C-C4), benzyl, cycloalkyl (C3C6) or phenyl, each of the symbols Het ³ and Het ⁴ independently represents between

37/289 si, a morpholino, piperidine or pyrrolidine group and the symbol n represents 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2, 3 or 4 and in particular 0, 1, 2 or 3.

[090] Here, compounds (I) are more preferred, where the symbol (R ² ) n represents n substituents R ² , where the substituent R ² , if n = 1, or each of the substituents R ² , if n is greater than 1, independently represents halogen, cyano, nitro, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, (C1-C2) alkylsulfinyl, (C1C2) alkylsulfonyl, haloalkyl (C1-C2), haloalkoxy (C1-C2), haloalkyl (C1-C2) -thio, haloalkyl (C1-C2) -sulfinyl, haloalkyl (C1-C2) -sulfonyl or alkoxy (C1-C2) -alkyl (CiC2 ), in particular, each of the R ² substituents independently represents halogen, such as fluorine, chlorine, bromine or iodine, or cyano, nitro, methyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl, trifluoromethyl, trifluoromethoxy , trifluoroalkylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl and, in particular, halogen, such as fluorine, chlorine or bromine, and n represents 0, 1, 2, 3, 4 or 5, preferably 0, 1, 2, 3 or 4 is at particular 0, 1, 2 or 3.

[091] Even more preferred are compounds of formula (I), or their salts, where the symbol is 0 (= the number zero, that is, no R ² substituents are present, that is, all free bonds of the ring are occupied by hydrogen) or, preferably, the symbol (R ² ) n represents 2-bromine, 3-bromine, 4-bromine, 2-chlorine, 3-chlorine, 4-chlorine,

2- fluorine, 3-fluorine, 4-fluorine, 2-cyano, 3-cyano, 4-cyano, 2-methyl, 3-methyl, 4-methyl, 2-ethyl, 3-ethyl, 4-ethyl, 2-CF3, 3-CF3, 4-CF3, 2-methoxy, 3-methoxy, 4-methoxy, 2-ethoxy,

3-ethoxy, 4-ethoxy, 2-methylthio, 3-methylthio, 4-methylthio, 2-methylsulfinyl, 3-methylsulfinyl, 4-methylsulfinyl, 2-methylsulfonyl, 3-methylsulfonyl, 4-methylsulfonyl, 2-nitro, 3-nitro, 4nitro, 2,3-dimethyl, 2,4-dimethyl, 2,5-dimethyl, 2,6-dimethyl, 3,4-dimethyl, 3,538 / 289 dimethyl, 2,3-difluoro, 2,4-difluoro, 2 , 5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro, 2,3dichloro, 2,4-dichloro, 2,5-dichloro, 2,6-dichloro, 3,4-dichloro , 3,5-dichloro, (2-Cl-3-F), (2Cl-4-F), (2-Cl-5-F), (2-Cl-6-F), (3-Cl- 2-F), (3-Cl-4-F), (3-Cl-5-F), (3-Cl-6-F), (4-Cl2-F), (4-Cl-3- F), 2,3,4-trifluoro, 2,3,5-trifluoro, 2,3,6-trifluoro, 2,4,6-trifluoro, 3,4,5trifluoro, 2,3,4-trichloro, 2 , 3,5-trichloro, 2,3,6-trichloro, 2,4,6-trichloro, 3,4,5-trichloro or else 2-nitro, 3-nitro, 4-nitro, 2,5-diciano, 2,6-diciano, (4-Br-2-F), (4-Br-3-F), (4CN-3-F), (4-nitro-3-F), (4-methoxy-3 -F), (3-cyano-4-F), (3-nitro-4-F), (3-cyano-4-Cl), (3-nitro-4-Cl) or (5-cyano-2 -F), where the numbering of the radicals refers to the position of the radical in the phenyl-1-yl radical in which the carbon atom attached to position 3 of the valeronitrile backbone has position 1 in the ring.

[092] Even more preferred are compounds of formula (I), or their salts, where (R ² ) n represents 2-bromine, 3-bromine, 4-bromine, 2-chlorine, 3-chlorine, 4-chlorine,

2- fluorine, 3-fluorine, 4-fluorine, 2-nitro, 3-nitro, 4-nitro, 2-methoxy, 3-methoxy, 4-methoxy, 2,3-fluorine, 2,4-difluorine, 2,5- difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro, 2,3-dichloro, 2,4dichloro, 2,5-dichloro, 2,6-dichloro, 3,4-dichloro, 3, 5-dichloro, (2-Cl-3-F), (2-Cl-4-F), (2Cl-5-F), (2-Cl-6-F), (3-Cl-2-F ), (3-Cl-4-F), (3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F), (4-Cl3-F), 2,3,4-trifluoro, 2,3,5-trifluoro, 2,3,6-trifluoro, 2,4,6-trifluoro, 3,4,5-trifluoro, 2,3,4trichloro, 2,3, 5-trichloro, 2,3,6-trichloro, 2,4,6-trichloro, 3,4,5-trichloro or 2-nitro,

3-nitro, 4-nitro, 2,5-diciano, 2,6-diciano, (4-Br-2-F), (4-Br-3-F), (4-CN-3-F), (4NO2-3-F), (4-OMe-3-F), (3-CN-4-F), (3-NO2-4-F), (3-CN-4-Cl), (3 -NO2-4-Cl) or (5-CN-2-F).

[093] Also more preferred are compounds of formula (I), or their salts, in which (R ² ) n represents 3-chlorine, 4-chlorine, 2-fluorine, 3-fluorine, 4-fluorine, 2,3-difluoro,

2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro, 3,4-dichloro, 3,5-dichloro, (3-Cl-2-F ), (3-Cl-4-F), (3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F), (4-Cl-3-F ).

[094] Here, they are particularly preferred:

compounds of formula (I), or their salts, wherein (R ² ) does not represent 3-chlorine;

39/289 compounds of formula (I) represents 4-chlorine; compounds of formula (I) represent 2-fluorine;

compounds of formula (I) represent 3-fluorine;

compounds of formula (I) represent 4-fluorine;

compounds of formula (I) represent 2,3-difluoro; compounds of formula (I) represent 2,4-difluoro; compounds of formula (I) represent 2,5-difluoro; compounds of formula (I) represent 2,6-difluoro; compounds of formula (I) represent 3,4-difluoro; compounds of formula (I) represent 3,5-difluoro; compounds of formula (I) represent (3-Cl-2-F); compounds of formula (I) represent (3-Cl-4-F); compounds of formula (I) represent (3-Cl-5-F); compounds of formula (I) represent (3-Cl-6-F); compounds of formula (I) represent (4-Cl-2-F);

or its salts, in or its salts, in or its salts, in or its salts, in or its salts, in or its salts, in or its salts, in or its salts, in or its salts, in or their salts, in or their salts, in or their salts, in or their salts, in or their salts, where the symbol (R ² ) n that the symbol (R ² ) n that the symbol (R ² ) n that the symbol (R ² ) n that the symbol (R ² ) n that the symbol (R ² ) n that the symbol (R ² ) n that the symbol (R ² ) n that the symbol (R ² ) n that the symbol (R ² ) n that the symbol (R ² ) n that the symbol (R ² ) n that the symbol (R ² ) n that the symbol (R ² ) n that the symbol (R ² ) n

40/289 compounds of structural formula (I), or their salts, in which the symbol (R ² ) does not represent (4-Cl-3-F).

[095] Even more preferred are:

compounds of formula (I), or their salts, where m = 0 and the symbol (R ² ) n represents 3-chlorine, 4-chlorine, 2-fluorine, 3-fluorine, 4-fluorine, 2,3- difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro, (3-Cl-2-F), (3-Cl-4-F), (3-Cl-5-F), (3-Cl6-F), (4-Cl-2-F) or (4-Cl-3-F);

compounds of formula (I), or their salts, in which the symbol (R ¹ ) m represents 3-chlorine and the symbol (R ² ) n represents 3-chlorine, 4-chlorine, 2-fluorine, 3-fluorine,

4-fluorine, 2,3-difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro, (3Cl-2-F), (3 -Cl-4-F), (3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F) or (4-Cl-3-F);

compounds of formula (I), or their salts, in which the symbol (R ¹ ) m represents 4-chlorine and the symbol (R ² ) n represents 3-chlorine, 4-chlorine, 2-fluorine, 3-fluorine,

4-fluorine, 2,3-difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro, (3Cl-2-F), (3 -Cl-4-F), (3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F) or (4-Cl-3-F);

compounds of formula (I), or their salts, in which the symbol (R ¹ ) m represents 3-fluorine and the symbol (R ² ) n represents 3-chlorine, 4-chlorine, 2-fluorine, 3-fluorine,

4-fluorine, 2,3-difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro, (3Cl-2-F), (3 -Cl-4-F), (3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F) or (4-Cl-3-F);

compounds of formula (I), or their salts, in which the symbol (R ¹ ) m represents (3-CN-4-F) and the symbol (R ² ) n represents 3-chloro, 4-chloro, 2- fluorine, 3-fluorine, 4-fluorine, 2,3-difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro, (3-Cl-2 -F), (3-Cl-4-F), (3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F) or (4-Cl-3 -F); compounds of formula (I), or their salts, in which the symbol (R ¹ ) m represents (3-Br-4-F) and the symbol (R ² ) n represents 3-chloro, 4-chloro, 2- fluorine, 3-fluorine, 4-fluorine, 2,3-difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro, (3-Cl-2 -F), (3-Cl-4-F), (3-Cl-5-F), (3-Cl-6-F), (4-Cl-2-F) or (4-Cl-3 -F); compounds of structural formula (I), or their salts, in which the symbol (R ¹ ) m represents 4-fluorine and the symbol (R ² ) n represents 3-chlorine, 4-chlorine, 2-fluorine, 3-fluorine,

4-fluorine, 2,3-difluoro, 2,4-difluoro, 2,5-difluoro, 2,6-difluoro, 3,4-difluoro, 3,5-difluoro, (341/289

CI-2-F), (3-CI-4-F), (3-CI-5-F), (3-CI-6-F), (4-CI-2-F) or (4- CI-3-F);

compounds of structural formula (I), or their salts, in which the symbol (R ¹ ) m represents 3-cyano and the symbol (R ² ) n represents 3-chloro, 4-chloro, 2-fluor, 3-fluor,

4-fluor, 2,3-difluor, 2,4-difluor, 2,5-difluor, 2,6-difluor, 3,4-difluor, 3,5-difluor, (3CI-2-F), (3 -CI-4-F), (3-CI-5-F), (3-CI-6-F), (4-CI-2-F) or (4-CI-3-F);

compounds of formula (I), or their salts, in which the symbol (R ¹ ) m represents 3,4-difluor and the symbol (R ² ) n represents 3-chloro, 4-chloro, 2-fluor, 3 fluorine, 4-fluor, 2,3-difluor, 2,4-difluor, 2,5-difluor, 2,6-difluor, 3,4-difluor, 3,5-difluor, (3-CI-2-F), (3-CI-4-F), (3-CI-5-F), (3-CI-6-F), (4-CI-2-F) or (4-CI-3-F); compounds of structural formula (I), or their salts, in which the symbol (R ¹ ) m represents 3,4-dichloro and the symbol (R ² ) n represents 3-chloro, 4-chloro, 2-fluor, 3 fluorine, 4-fluor, 2,3-difluor, 2,4-difluor, 2,5-difluor, 2,6-difluor, 3,4-difluor, 3,5-difluor, (3-CI-2-F), (3-CI-4-F), (3-CI-5-F), (3-CI-6-F), (4-CI-2-F) or (4-CI-3-F); compounds of formula (I), or their salts, in which the symbol (R ¹ ) m represents 3,5-difluor and the symbol (R ² ) n represents 3-chloro, 4-chloro, 2-fluor, 3 fluorine, 4-fluor, 2,3-difluor, 2,4-difluor, 2,5-difluor, 2,6-difluor, 3,4-difluor, 3,5-difluor, (3-CI-2-F), (3-CI-4-F), (3-CI-5-F), (3-CI-6-F), (4-CI-2-F) or (4-CI-3-F); compounds of formula (I), or their salts, in which the symbol (R ¹ ) m represents 3,5-dichloro and the symbol (R ² ) n represents 3-chloro, 4-chloro, 2-fluor, 3-fluorine, 4-fluor, 2,3-difluor, 2,4-difluor, 2,5-difluor, 2,6-difluor, 3,4-difluor, 3,5-difluor, (3-CI-2-F), (3-CI-4-F), (3-CI-5-F), (3-CI-6-F), (4-CI-2-F) or (4-CI-3-F); compounds of formula (I), or their salts, in which the symbol (R ¹ ) m represents (3-CI-4-F) and the symbol (R ² ) n represents 3-chloro, 4-chloro, 2- fluorine, 3-fluorine, 4-fluorine, 2,3-difluor, 2,4-difluor, 2,5-difluor, 2,6-difluor, 3,4-difluor, 3,5-difluor, (3-CI-2 -F), (3-CI-4-F), (3-CI-5-F), (3-CI-6-F), (4-CI-2-F) or (4-CI-3 -F). compounds of formula (I), or their salts, in which the symbol (R ¹ ) m represents (4-CI-3-F) and the symbol (R ² ) n represents 3-chloro, 4-chloro, 2- fluorine, 3-fluorine, 4-fluorine, 2,3-difluor, 2,4-difluor, 2,5-difluor, 2,6-difluor, 3,4-difluor, 3,5-difluor, (3-CI-2 -F), (3-CI-4-F), (3-CI-5-F), (3-CI-6-F), (4-CI-2-F) or (4-CI-3 -F).

[096] Also preferred are:

42/289 compounds of structural formula (I), or their salts, where n = 0 and the symbol (R ¹ ) m represents 3-chlorine, 4-chlorine, 3-fluorine, 4-fluorine, 3-cyano, 3 , 4-difluoro, 3,5-difluoro, 3,4dichloro, 3,5-dichloro, (3-Cl-4-F), (3-Cl-5-F) or (4-Cl-3-F) or (3-CN-4-F), (3Br-4-F);

compounds of formula (I), or their salts, in which the symbol (R ² ) n represents 3-chlorine and the symbol (R ¹ ) n represents 3-chlorine, 4-chlorine, 3-fluorine, 4-fluorine, 3-cyano, 3,4-difluoro, 3,5-difluoro, 3,4-dichloro, 3,5-dichloro, (3-Cl-4-F), (3-Cl-5-F) or (4 -Cl-3-F) or (3-CN-4-F), (3-Br-4-F);

compounds of formula (I), or their salts, in which the symbol (R ² ) n represents 4-chlorine and the symbol (R ¹ ) m represents 3-chlorine, 4-chlorine, 3-fluorine, 4-fluorine, 3-cyano, 3,4-difluoro, 3,5-difluoro, 3,4-dichloro, 3,5-dichloro, (3-Cl-4-F), (3-Cl-5-F) or (4 -Cl-3-F) or (3-CN-4-F), (3-Br-4-F);

compounds of formula (I), or their salts, in which the symbol (R ² ) n represents 3-fluorine and the symbol (R ¹ ) m represents 3-chlorine, 4-chlorine, 3-fluorine, 4-fluorine, 3-cyano, 3,4-difluoro, 3,5-difluoro, 3,4-dichloro, 3,5-dichloro, (3-Cl-4-F), (3-Cl-5-F) or (4 -Cl-3-F) or (3-CN-4-F), (3-Br-4-F);

compounds of structural formula (I), or their salts, in which the symbol (R ² ) n represents 4-fluorine and the symbol (R ¹ ) m represents 3-chlorine, 4-chlorine, 3-fluorine, 4-fluorine, 3-cyano, 3,4-difluoro, 3,5-difluoro, 3,4-dichloro, 3,5-dichloro, (3-Cl-4-F), (3-Cl-5-F) or (4 -Cl-3-F) or (3-CN-4-F), (3-Br-4-F);

compounds of structural formula (I), or their salts, in which the symbol (R ² ) n represents 2,3-difluoro and the symbol (R ¹ ) m represents 3-chloro, 4-chloro, 3-fluoro, 4fluor, 3-cyano, 3,4-difluoro, 3,5-difluoro, 3,4-dichloro, 3,5-dichloro, (3-Cl-4-F), (3-Cl-5F) or (4-Cl -3-F) or (3-CN-4-F), (3-Br-4-F);

compounds of formula (I), or their salts, in which the symbol (R ² ) n represents 2,4-difluoro and the symbol (R ¹ ) m represents 3-chloro, 4-chloro, 3-fluoro, 4fluor, 3-cyano, 3,4-difluoro, 3,5-difluoro, 3,4-dichloro, 3,5-dichloro, (3-Cl-4-F), (3-Cl-5F) or (4-Cl -3-F) or (3-CN-4-F), (3-Br-4-F);

compounds of formula (I), or their salts, in which the symbol (R ² ) n represents 2,5-difluoro and the symbol (R ¹ ) m represents 3-chloro, 4-chloro, 3-fluoro, 443 / 289 fluorine, 3-cyano, 3,4-difluoro, 3,5-difluoro, 3,4-dichloro, 3,5-dichloro, (3-CI-4-F), (3-CI-5F) or ( 4-Cl-3-F) or (3-CN-4-F), (3-Br-4-F);

compounds of formula (I), or their salts, in which the symbol (R ² ) n represents 2,6-difluoro and the symbol (R ¹ ) m represents 3-chloro, 4-chloro, 3-fluoro, 4fluor, 3-cyano, 3,4-difluoro, 3,5-difluoro, 3,4-dichloro, 3,5-dichloro, (3-Cl-4-F), (3-Cl-5F) or (4-Cl -3-F) or (3-CN-4-F), (3-Br-4-F);

compounds of formula (I), or their salts, in which the symbol (R ² ) n represents 3,4-difluoro and the symbol (R ¹ ) m represents 3-chloro, 4-chloro, 3-fluoro, 4fluor, 3-cyano, 3,4-difluoro, 3,5-difluoro, 3,4-dichloro, 3,5-dichloro, (3-Cl-4-F), (3-Cl-5F) or (4-Cl -3-F) or (3-CN-4-F), (3-Br-4-F);

compounds of formula (I), or their salts, in which the symbol (R ² ) n represents 3,5-difluoro and the symbol (R ¹ ) m represents 3-chloro, 4-chloro, 3-fluoro, 4fluor, 3-cyano, 3,4-difluoro, 3,5-difluoro, 3,4-dichloro, 3,5-dichloro, (3-Cl-4-F), (3-Cl-5F) or (4-Cl -3-F) or (3-CN-4-F), (3-Br-4-F);

compounds of formula (I), or their salts, in which the symbol (R ² ) n represents (3-Cl-2-F) and the symbol (R ¹ ) m represents 3-chloro, 4-chloro, 3- fluorine, 4-fluorine, 3-cyano, 3,4-difluoro, 3,5-difluoro, 3,4-dichloro, 3,5-dichloro, (3-Cl-4-F), (3-Cl-5F) or (4-Cl-3-F) or (3-CN-4-F), (3-Br-4-F);

compounds of formula (I), or their salts, in which the symbol (R ² ) n represents (3-Cl-4-F) and the symbol (R ¹ ) m represents 3-chloro, 4-chloro, 3- fluorine, 4-fluorine, 3-cyano, 3,4-difluoro, 3,5-difluoro, 3,4-dichloro, 3,5-dichloro, (3-Cl-4-F), (3-Cl-5F) or (4-Cl-3-F) or (3-CN-4-F), (3-Br-4-F);

compounds of formula (I), or their salts, in which the symbol (R ² ) n represents (3-Cl-5-F) and the symbol (R ¹ ) m represents 3-chloro, 4-chloro, 3- fluorine, 4-fluorine, 3-cyano, 3,4-difluoro, 3,5-difluoro, 3,4-dichloro, 3,5-dichloro, (3-Cl-4-F), (3-Cl-5F) or (4-Cl-3-F) or (3-CN-4-F), (3-Br-4-F);

compounds of formula (I), or their salts, in which the symbol (R ² ) n represents (3-Cl-6-F) and the symbol (R ¹ ) m represents 3-chloro, 4-chloro, 3- fluorine, 4-fluorine, 3-cyano, 3,4-difluoro, 3,5-difluoro, 3,4-dichloro, 3,5-dichloro, (3-Cl-4-F), (3-Cl-5F) or (4-Cl-3-F) or (3-CN-4-F), (3-Br-4-F);

44/289 compounds of structural formula (I), or their salts, in which the symbol (R ² ) n represents (4-Cl-2-F) and the symbol (R ¹ ) m represents 3-chlorine, 4-chlorine , 3-fluorine, 4-fluorine, 3-cyano, 3,4-difluoro, 3,5-difluoro, 3,4-dichloro, 3,5-dichloro, (3-Cl-4-F), (3-Cl- 5F) or (4-Cl-3-F) or (3-CN-4-F), (3-Br-4-F);

compounds of formula (I), or their salts, in which the symbol (R ² ) n represents (4-Cl-3-F) and the symbol (R ¹ ) m represents 3-chloro, 4-chloro, 3- fluorine, 4-fluorine, 3-cyano, 3,4-difluoro, 3,5-difluoro, 3,4-dichloro, 3,5-dichloro, (3-Cl-4-F), (3-Cl-5F) or (4-Cl-3-F) or (3-CN-4-F), (3-Br-4-F).

[097] More preferred are compounds of formula (I), or their salts, 10 where m = 1.

[098] More preferred are compounds of formula (I), or their salts, where m = 1 and the symbol R ² represents halogen, such as fluorine or chlorine. [099] More preferred are compounds of formula (I), or their salts, where m = 2 or 3 and, in particular, 2.

[100] The compounds of structural formula (I), or their salts, are more preferred, where m = 2 and each of the symbols R ² is selected from the group consisting of halogen, preferably fluorine or chlorine, and in particular , fluorine.

[101] In general, among the compounds that have the above meanings for individual groups or for combinations of groups (R ¹ ) m and / or (R ² ) n, those in which the remaining groups or where the combinations are preferred groups in the compounds are defined according to the meanings mentioned as preferred.

[102] Compounds (I) are also preferred, in which L represents a radical of structural formula A ¹

B ^{1 ,} the symbol A ¹ represents oxygen, sulfur or = NR ^A and, preferably, oxygen, the symbol B ¹ represents a radical of structural formulas (B1) to (B14) referred to, the symbol R ^A has the meaning defined above and preferably represents

45/289 hydrogen, hydroxy, alkoxy (C1-C4), alkyl (C1-C4), haloalkyl (C1-C4), phenyl which is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1C4), haloalkoxy (C1-C4), or benzyl which is unsubstituted in the phenyl residue or is substituted with one or more radicals selected from the group consisting of halogen, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1-C4), haloalkoxy (C1C4), or -NR * R **, where each of the symbols R *, R ** represents, of independently, H, alkyl (C-C4), alkenyl (C2-C4), alkynyl (C2-C4), alkoxy (C-C4) -alkyl (C-C4), alkanoyl (C-C4), [haloalkyl (C1-C4)] - carbonyl, [alkoxy (C1-C4)] - carbonyl, [haloalkoxy (C1-C4)] - carbonyl, cycloalkyl (C3-C6), cycloalkyl (C3-Ce) -alkyl (Ci -C4), phenyl, phenyl-alkyl (C1-C4), where each of these last 4 radicals is unsubstituted in the cycle or is substituted with one or more radicals selected from the set made up of halogen, alkyl (C4), haloalkyl (C1-C4), alkoxy (C1-C4) or haloalkoxy (C1-C4), or, in the case of cycloalkyl, also with oxo, or the symbols R * and R **, together with the nitrogen atom, represent a 3- to 6-membered and preferably saturated heterocycle, which, in addition to the nitrogen atom, may contain one or two other hetero atoms in the ring of the set consisting of N , O and S, and which can be unsubstituted or substituted with one or more radicals selected from the group consisting of alkyl (C1-C4), haloalkyl (C1-C4) and oxo, in particular, the symbol R ^A represents hydrogen, (C 1 -C 4) alkyl, phenyl, benzyl or -NR * R **, where each of the symbols R *, R ** independently represents H or C 1 -C 4 alkyl, the symbols (R ⁱ ) m, (R ² ) n, R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ⁱ⁰ , R, R ⁱ² , R ⁱ³ , R ⁱ⁴ , R ⁱ⁵ , R ⁱ⁶ , R ⁱ⁷ , R ⁱ⁸ , R ⁱ⁹ , R ²⁰ , R ^{2 1} , R ²² , R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ , R ²⁸ , R ²⁹ , R ³⁰ , R ^{3 1} and R ³² have the meanings or preferred meanings defined above, each of the symbols W ⁱ and W ⁶ independently represents the divalent oxygen, sulfur group or a group of the general formula NH, N [alkyl (Ci-C4)], C = O, S = O, SO2 or CR ³⁵ R ³⁶ ,

46/289 each of the symbols W ² , W ³ , W ⁴ , W ⁵ and W ⁷ independently represents the divalent group of general formula O, S, NH, N- [(C C4) alkyl ], C = O, S = O or SO2, each of the symbols Q ¹ , Q ² , Q ³ , Q ⁴ , Q ⁵ , Q ⁶ , Q ⁷ , Q ⁸ and Q ⁹ represents, independently of each other , hydroxy, uncle, halogen or a group of general formula OR ³⁷ , SR ³⁸ , SM or OM, the symbol M represents an equivalent of a cation, each of the symbols R ³⁵ and R ³⁶ has, independently of each other, the meaning defined for the symbol R ³ or, preferably, independently represents H, alkyl (C 1 -C 4) or haloalkyl (C 1 -C 4), preferably H or alkyl (C 1-C 2) and, in particular, H, methyl or ethyl, the symbols R ³⁷ , R ³⁸ , R ⁶⁶ , R ⁶⁷ , R ⁶⁸ , R ⁶⁹ , R ⁷⁰ , R ⁷¹ , Het ¹² and M have the meanings mentioned above and, preferably, each one of the symbols R ³⁷ and R ³⁸ independently represents (C1-C6) alkyl, haloalkyl (C1-C6), alkoxy (C1-C4) -al kyl (C1-C4), cycloalkyl (C3C6) which is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, alkyl (C-C4) and alkoxy (C-C4), phenyl which is unsubstituted or is substituted with one or more radicals selected from the group consisting of halogen, cyano, hydroxy, nitro, alkyl (C1-C4), haloalkyl (C1-C4) and alkoxy (C1-C4), or a group of general formula - C (O) R ⁶⁷ , C (O) OR ⁶⁸ , -C (O) NR ⁶⁹ R ⁷⁰ , -C (O) Het ⁱ² or -SO2R ⁷ i in particular, each of the symbols R ³⁷ and R ³⁸ represents, independently of one another, alkyl (C-C6), haloalkyl (C-C4), cycloalkyl (C3-C6), halocycloalkyl (C3-C6), phenyl which is unsubstituted or substituted with one or more radicals selected from the set consisting of halogen and (C 1 -C 4) alkyl, or a group of general formula -C (O) R ⁶⁷ , -C (O) OR ⁶⁸ , C (O) NR ⁶⁹ R ⁷⁰ , -C (O) Het ⁱ² or -SO2R ^{7 the} symbol R ⁶⁷ represents hydrogen, (C1-C6) alkyl, haloalkyl (C1-C4), phenyl or benzyl, where ca of one of these last 2 radicals, independently of each other, is unsubstituted or is substituted with one or more selected radicals

47/289 between the group consisting of halogen, cyano, alkyl (C1-C4) and haloalkyl (C1C4) and, in particular, H or alkyl (C1-C4), the symbol R ⁶⁸ represents alkyl (C1-C) or haloalkyl (C1-C4) and, in particular, (C1-C4) alkyl, each of the symbols R ⁶⁹ and R ⁷⁰ independently represents hydrogen, alkyl (C-C4), benzyl, cycloalkyl (C3- C6) or phenyl, in which each of these last 2 radicals, independently of each other, is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, nitro, cyano, alkyl (C1-C4) and haloalkyl (C1-C4) and, in particular, each independently represents H or alkyl (C1-C3), the symbol R ^{7 1} represents alkyl (C1-C4), haloalkyl (C1-C4) ), phenyl or benzyl, in which each of these last 2 radicals, independently of each other, is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, cyano, alkyl ( C1-C4), alkenyl (C2-C4) and haloalkyl (C1-C4) and, in particular, alkyl (C1-C4), haloalkyl (C1-C4), benzyl or phenyl which is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, alkyl (C-C4) and haloalkyl (C-C4), the symbol Het ⁱ² represents a saturated or partially unsaturated radical of a heterocycle that has 3 to 6 ring atoms and at least one nitrogen atom as ring hetero atom in position 1 of the ring and, optionally, 1, 2 or 3 other ring hetero atoms of the set consisting of N, O and S, where the radical of the heterocycle in the nitrogen atom in position 1 of the ring is attached to the remainder of the molecule of the compound of structural formula (I) and in which the heterocycle is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, alkyl (C-C4), haloalkyl (Ci- C4), alkoxy (C1-C4), haloalkoxy (C1-C4), alkyl (C1-C4) -thio and oxo and, in particular, is unsubstituted or is substituted with one or more radicals selected from the group consisting of alkyl (C1-C4) and haloalkyl (C1-C4),

48/289 in particular a morpholino, piperidine or pyrrolidine group, and the symbol M represents an equivalent of a cation, preferably an equivalent to a metal ion, an ammonium ion which is optionally substituted with 1 to 4 radicals, the same or different , selected from the group consisting of alkyl (C-C4), cycloalkyl (C3-C6), phenyl, cycloalkyl (C3-C6) alkyl (C1-C4) and phenyl-alkyl (C1-C4), in particular alkyl (Ci -C4), or a tertiary sulfonium ion that is preferably substituted with 3 radicals, the same or different, selected from the group consisting of alkyl (C-C4), cycloalkyl (C3-C6), phenyl, cycloalkyl (C3-C6) - alkyl (C 1 -C 4) and phenyl-alkyl (C 1 -C 4), in particular alkyl (C 1 -C 4).

[103] Compounds (I) are also preferred, in which the symbol B ⁱ represents a radical of the structural formulas (B1) to (B14) mentioned, each of the symbols R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ⁱ⁰ , R, R ⁱ² , R ⁱ³ , R ⁱ⁴ , R ⁱ⁵ , R ⁱ⁶ , R ⁱ⁷ , R ⁱ⁸ , R ⁱ⁹ and R ²⁰ represent, independently of each other, H, halogen, cyano, nitro, hydroxy, alkyl (C1-C4), haloalkyl (C1-C4), cycloalkyl (C3-C6), alkoxy (C1-C4) or haloalkoxy (C1-C4) and, in particular, H or alkyl (Ci-C4), or the symbols R ³ and R ⁵ , in the group of structural formula (B1), together, represent a divalent bridge as defined above, the symbol R ^{2 1} represents H, alkyl (Ci-C4) , haloalkyl (C1-C4), cycloalkyl (C3Ce), halocycloalkyl (C3-C6) or a group C (O) OR ⁵⁴ , C (O) NR ⁵⁵ R ⁵⁶ , C (O) Het ⁷ , NR ⁵⁷ R ⁵⁸ or Het ⁸ and, preferably, (C1-C4) alkyl, haloalkyl (C1-C4), cycloalkyl (C3-C6) or a C (O) OR ^{54 group} , the symbol R ²² represents H, (C1-C4) alkyl , haloalkyl (C1-C4), cycloalkyl (C3C6), halocycloalk uyl (C3-C6), (C1-C4) alkylthio, (C1-C4) alkylsulfonyl or a group of the general formula C (O) OR ⁵⁹ , C (O) NR ⁶⁰ R ⁶ⁱ , C (O) Het ⁹ , NR ⁶² R ⁶³ or Het ⁱ⁰ and preferably (C1-C4) alkyl, haloalkyl (C1-C4), cycloalkyl (C3-C6), alkyl (C1-C4) sulfonyl or a C (O) group R ⁵⁹ , each of the symbols R ²³ and R ²⁹ independently represents H, alkyl (C-C4), haloalkyl (C-C4), cycloalkyl (C3-C6), halocycloalkyl (C3-C6) ,

49/289 alkoxy (C1-C4) or haloalkoxy (C1-C4) and preferably H, alkyl (C1-C4), haloalkyl (C1-C4), cycloalkyl (C3-C6), for example, cyclopropyl, alkoxy (C1-C4) or haloalkoxy (C1-C2), each of the symbols R ²⁴ and R ³⁰ independently represents H, halogen, cyano, alkyl (C1-C4), haloalkyl (C1-C4) , cycloalkyl (C3-C6), alkoxy (C1-C4) or haloalkoxy (C1-C4), and preferably H, halogen, cyano, alkyl (C1-C4), haloalkyl (C1-C4), cycloalkyl (C3- C6), for example, cyclopropyl, alkoxy (C1-C4) or haloalkoxy (C1-C2), each of the symbols R ²⁵ , R ²⁶ , R ^{3 1} and R ³² independently represents H, alkyl (C1-C4), halo (C1-C4), alkoxy (C1-C4), haloalkoxy (C1-C4), alkoxy (C1-C4) -alkyl (C1-C4), haloalkoxy (C1-C4) -alkyl ( C1-C4), cycloalkyl (C3C6), cycloalkoxy (C3-C6), alkenyl (C2-C6), alkynyl (C2-C6), alkyl (C2-C6) -thio, alkyl (C1-C6) -sulfonyl, NR ⁶⁴ R ⁶⁵ or Hei ^{1 1} and preferably H, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1-C4), haloalkoxy (Ci -C4), alkoxy (C1-C2) -alkyl (C1-C2), haloalkoxy (C1-C2) -alkyl (C1-C2) or cycloalkyl (C3-C6), for example, cyclopropyl, the symbol R ²⁷ represents H , (C1-C4) alkyl, halo (C1-C4) or cycloalkyl (C3C6), for example, cyclopropyl, and preferably H or (C1-C3) alkyl, R ²⁸ represents H, alkyl (C1-6) C4), haloalkyl (C1-C4) or a radical of the general formula C (O) OR ⁶⁶ and, preferably, H or alkyl (C1-C3), each of the symbols R ⁵⁴ , R ⁵⁹ and R ⁶⁶ represents, independently, H, alkyl (C-C4), haloalkyl (C-C4), cycloalkyl (C3-C6), alkenyl (C2-C4), alkynyl (C2-C4) or the mentioned group M preferably H or (C1 -C3) alkyl, each of the symbols R ⁵⁵ , R ⁵⁶ , R ⁵⁷ , R ⁵⁸ , R ⁶⁰ , R ^{6 1} , R ⁶² , R ⁶³ , R ⁶⁴ and R ⁶⁵ represents, in a different way independent of each other, H, (C1 -C4) alkyl which is unsubstituted or is substituted with one or more radicals selected from the group consisting of halogen, nitro, cyano and phenyl which is unsubstituted or is substituted with one or more radicals selected from the group consisting of halogen, nitro, cyano, alkyl (C-C4) and haloalkyl (C1-C4), or cycloalkyl (C3-C6) which is unsubstituted or is replaced with one or more radicals selected from the group consisting of halogen and alkyl (C1-C4)

50/289 and haloalkyl (Ci-C4), or phenyl which is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, nitro, cyano, alkyl (Ci C4) and haloalkyl (Ci-C4), each of the symbols Het ⁷ , Het ⁸ , Het ⁹ , Het ¹⁰ and Het ¹¹ independently represents a saturated or partially unsaturated radical of a heterocycle that has 3 to 6 ring atoms and at least one atom nitrogen as ring heteroatom at position 1 of the ring and, optionally,

1,2 or 3 other ring hetero atoms of the set consisting of N, O and S, where the radical of the heterocycle in the nitrogen atom at position 1 of the ring is attached to the remainder of the molecule of the compound of formula (I) and wherein the heterocycle is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1-C4), haloalkoxy (C1-C4) , (C1 -C4) alkylthio and oxo and, in particular, is unsubstituted or substituted with one or more radicals selected from the group consisting of (C1-C4) alkyl and (C1-C4) haloalkyl, in particular, one morpholino, piperidine or pyrrolidine group.

[104] In this case, compounds (I) are preferred, in which the symbol B ⁱ represents a radical (B1)

R ⁴ (B1) and that the symbols W ⁱ , Q ⁱ , R ³ , R ⁴ , R ⁵ and R ⁶ have the preferred meanings or meanings mentioned above and, preferably, the symbol W ⁱ represents the divalent group of formula general O, S, NH, N [(C-C4 alkyl)], C = O, S = O, SO2 or CR ³⁵ R ³⁶ and, in particular, the divalent group of general formula O, S, C = O or CR ³⁵ R ³⁶ , in which each of the symbols R ³⁵ and R ³⁶ represents, independently

51/289 with each other, hydrogen, (C1-C4) alkyl or haloalkyl (C1-C4), in particular, the symbol W ¹ represents the divalent group C (O), CH2, CH (CH3) or C (CH3) 2 , Q ¹ represents hydroxy, thio, halogen or a group of general formula OR ³⁷ , SR ³⁸ , SM or OM and, in particular, hydroxy, each of the symbols R ³ , R ⁴ , R ⁵ and R ⁶ represents, independently of each other, H, halogen, cyano, nitro, hydroxy, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1-C4) or haloalkoxy (C1-C4) and, in particular, H or (C 1 -C 4) alkyl, or the symbols R ³ and R ⁵ , together, represent a divalent bridge of general formula -CH2CH2-, -CH2CH2CH2-, -CH (CH3) CH2-, -C (CH3) 2CH2- , CH2CH (CH3) -, -CH2C (CH3) 2-, -C (CH3) CH (CH3) -, -CH2CH2CH2-, -CH = CH-, CH = CHCH2-, -CH2CH = CH-, -OCH2- , -CH2O-, -OCH2CH2-, -CH2OCH2-, CH2CH2O- or -OCH2O- and, in particular, of the general formula -CH2CH2- or -CH = CH ^, the symbols R ³⁷ , R ³⁸ , R ⁶⁷ , R ⁶⁸ , R ⁶⁹ , R ⁷⁰ , R ^{7 1} , Het ⁱ² and M have the meanings mentioned above and, preferably, c Each of the symbols R ³⁷ and R ³⁸ represents, independently from one another, alkyl (C 1 -C 6), haloalkyl (C 1 -C 6), alkoxy (C 1 -C 4) -alkyl (C 1 -C 4), cycloalkyl (C 3 C 6) which is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, alkyl (C-C4) and alkoxy (C-C4), phenyl which is unsubstituted or is substituted with one or more radicals selected from the group consisting of halogen, cyano, hydroxy, nitro, alkyl (C1-C4), haloalkyl (C1-C4) and alkoxy (C1-C4), or a group of general formula -C (O) R ⁶⁷ , C (O) OR ⁶⁸ , -C (O) NR ⁶⁹ R ⁷⁰ , -C (O) Het ^I2 or -SO2R ⁷ I and, in particular, each of the symbols R ³⁷ and R ³⁸ independently represents alkyl ( C1-C6), haloalkyl (C-C4), cycloalkyl (C3-C6), halocycloalkyl (C3-C6), phenyl which is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen and alkyl (Ci -C4), or a group of general formula -C (O) R ⁶⁷ , -C (O) OR ⁶⁸ , C (O) NR ⁶⁹ R ⁷⁰ , -C (O) Het ^I2 or -SO2R ⁷ I

52/289 and, more preferably, each of the symbols R ³⁷ and R ³⁸ independently represents (C 1 -C 4) alkyl, phenyl which is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen and (C1 -C4) alkyl, or a group of general formula -C (O) R ⁶⁷ , C (O) OR ⁶⁸ or -SO2R ⁷¹ , the symbol R ⁶⁷ represents hydrogen, (C1-C6) alkyl, haloalkyl (C1-C4), phenyl or benzyl, in which each of these last 2 radicals, independently of each other, is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, cyano, alkyl ( C1-4 and haloalkyl (C1-4) and, in particular, H or alkyl (C1-4), for example, H, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or t- butyl, the symbol R ⁶⁸ represents alkyl (C 1 -C 6) or haloalkyl (C 1 -C 4) and, in particular, alkyl (C 1 -C 4), each of the symbols R ⁶⁹ and R ⁷⁰ represents, independently of each other, hydrogen, alkyl (C i-C4), benzyl, cycloalkyl (C3-C6) or phenyl, in which each of these last 2 radicals, independently of each other, is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen , nitro, cyano, alkyl (C1-C4) and haloalkyl (C1-C4) or, in particular, independently represents H or alkyl (C1-C3), the symbol R ^{7 1} represents alkyl (Ci -C4), haloalkyl (C1-C4), phenyl or benzyl, in which each of these last 2 radicals, independently of each other, is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, cyano, alkyl (C1-C4), alkenyl (C2-C4) and haloalkyl (C1-C4) and, in particular, alkyl (C1-C4), haloalkyl (C1-C4), benzyl or phenyl which is unsubstituted or is substituted with one or more radicals selected from the group consisting of halogen, alkyl (C1-C4) and haloalkyl (C1-C4), the symbol Het ⁱ² represents a morpholino, piperidine or pyrrolidine and the symbol M represents an equivalent of a cation, preferably an equivalent of a metal ion, an ammonium ion that is optionally

53/289 substituted with 1 to 4 radicals, the same or different, selected from the group consisting of alkyl (C1-C4), cycloalkyl (C3-C6), phenyl, cycloalkyl (C3C6) -alkyl (C1-C4) and phenyl- alkyl (C1-C4) and, in particular, alkyl (C1-C4), or a tertiary sulfonium ion that is preferably substituted with 3 radicals, the same or different, selected from the group consisting of alkyl (C1-C4), cycloalkyl ( C3-C6), phenyl, cycloalkyl (C3-C6) -alkyl (C1-C4) and phenyl-alkyl (C1-C4) and, in particular, alkyl (C1-C4).

Examples of preferred B1 radicals of structural formula (B1) include the radicals of structural formulas (B1 -1) to (B1 -11):

54/289 [105] In structural formulas (B1-1) to (B1-11), the "methyl" substituents in the ring system are indicated, in conventional abbreviated notation, as a line extending from a carbon atom of the ring. This notation is also used in the subsequent structural formulas for the radicals B ¹ .

[106] The structural formula (B1-11) also covers tautomers, where the tautomer shown on the left is the thermodynamically more stable tautomer, whereas the tautomer shown on the right is the tautomer that formally corresponds exactly to the structural formula (B1), if Q ¹ = OH and W ¹ = C (O).

[107] In this case, compounds (I) are preferred, in which B ¹ represents a radical (B4)

O

Q (B4) that the symbols W ⁴ , W ⁵ , Q ⁴ , R ¹⁵ and R ¹⁶ have the meanings or preferred meanings mentioned above and, preferably, each of the symbols W ⁴ and W ⁵ independently represents the divalent group of the general formula O, S, NH, N- [(C1 -C4 alkyl)], C = O, S = O or SO2, in particular the divalent group of the general formula O or S and, in particular, O, the symbol Q ⁴ represents hydroxy, uncle, halogen or a group of general formula OR ³⁷ , SR ³⁸ , SM or OM and, in particular, hydroxy, each of the symbols R ¹⁵ and R ¹⁶ represents, from one independently of each other, H, halogen, cyano, nitro, hydroxy, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1C4) or haloalkoxy (C1-C4) and, in particular, hydrogen or alkyl (C1 -C4), the symbols R ³⁷ , R ³⁸ and M have the meanings mentioned above and, preferably, each of the symbols R ³⁷ and R ³⁸ independently represents (C1-C4) alkyl, haloalkyl ( C1-C4), alkoxy (C1-C4) -alkyl (C1-C4), cycloalkyl (C355 / 28 9

Ce) that is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, alkyl (C-C4) and alkoxy (Ci-C4), phenyl which is unsubstituted or is substituted with one or more selected radicals between the group consisting of halogen, cyano, hydroxy, nitro, alkyl (C1-C4), haloalkyl (C1-C4) and alkoxy (C1-C4), or a group of general formula -C (O) R ⁶⁷ , C ( O) OR ⁶⁸ , -C (O) NR ⁶⁹ R ⁷⁰ , -C (O) Het ⁱ² or -SO2R ⁷ i in particular, each of the symbols R ³⁷ and R ³⁸ independently represents alkyl ( C1-C6), haloalkyl (C-C4), cycloalkyl (C3-C6), halocycloalkyl (C3-C6), phenyl which is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen and alkyl (Ci -C4), or a group of general formula -C (O) R ⁶⁷ , -C (O) OR ⁶⁸ , C (O) NR ⁶⁹ R ⁷⁰ , -C (O) Het ⁱ² or -SO2R ⁷ ie, more preferably , each of the symbols R ³⁷ and R ³⁸ represents, independently of each other, (C 1 -C 4) alkyl, phenyl which is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen and (C 1 -C 4) alkyl, or a group of general formula -C (O) R ⁶⁷ , C (O) OR ⁶⁸ or -SO2R ⁷ \ the symbols R ⁶⁷ , R ⁶⁸ , R ⁶⁹ , R ⁷⁰ , R ^{7 1} , Het ⁱ² and M have the meanings mentioned above and, preferably, the symbol R ⁶⁷ represents hydrogen, alkyl (C1-C6), haloalkyl (C1-C4), phenyl or benzyl, in which each of these last 2 radicals, independently of each other, is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, cyano, (C1 -C4) alkyl and haloalkyl (C1C) and, in particular, H or alkyl (C1-C4), the symbol R ⁶⁸ represents alkyl (C1-C6) or haloalkyl (C1-C4) and, in in particular, alkyl (C1-C4), each of the symbols R ⁶⁹ and R ⁷⁰ independently represents hydrogen, alkyl (C1-C4), benzyl, cycloalkyl (C3-C6) or phenyl, where each one of these 2 latter radicals, independently of each other, is unsubstituted or is substituted with one or more radicals selected from the group

56/289 consisting of halogen, nitro, cyano, alkyl (C1-C4) and haloalkyl (C1-C4) or, in particular, each represents, independently of one another, H or alkyl (C1-C), the symbol R ⁷¹ represents alkyl (C1-C4), haloalkyl (C1-C4), phenyl or benzyl, in which each of these last 2 radicals, independently of each other, is unsubstituted or is substituted with one or more radicals selected from the group consisting of halogen, cyano, alkyl (C-C4), alkenyl (C2-C4) and haloalkyl (C1-C4) and, in particular, alkyl (C1-C4), haloalkyl (C1-C4), benzyl or phenyl that is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, alkyl (C-C4) and haloalkyl (C1-C4), the symbol Het ⁱ² represents a morpholino, piperidine or pyrrolidine group and the symbol M represents an equivalent of a cation and, preferably, an equivalent of a metal ion, an ammonium ion that is optionally substituted with 1 to 4 radicals, equal to u different, selected from the group consisting of alkyl (C1-C4), cycloalkyl (C3-C6), phenyl, cycloalkyl (C3Ce) -alkyl (C1-C4) and phenyl-alkyl (C1-C4) and, in particular, alkyl (C1-C4), or a tertiary sulfonium ion that is preferably substituted with 3 radicals, the same or different, selected from the group consisting of alkyl (C1-C4), cycloalkyl (C3-C6), phenyl, cycloalkyl (C3- C6) -alkyl (C1-C4) and phenyl-alkyl (C1-C4) and, in particular, alkyl (C1-C4).

[108] An example of a preferred B ⁱ radical of structural formula (B4) is the radical of structural formula (B4-1).

(B4-1)

HO O \ [109] Also preferred are compounds (I) in which the symbol B ⁱ represents a radical (B5) or (B6)

57/289

R ¹⁷

R ¹⁸

R i

(B6) in which the symbols W ⁶ , W ⁷ , Q ⁵ , Q ⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ have the meanings or preferred meanings mentioned above and, preferably, the symbol W ⁶ represents the divalent group of general formula O, S, NH, N [(C1 -C4 alkyl)], C = O, S = O, SO2 or a group of general formula CR ³⁵ R ³⁶ , in particular, the divalent group of general formula O, S, NH, N- [(C 1 -C 4 alkyl)] or a group of the general formula CR ³⁵ R ³⁶ , more preferably, O, NH, N-CH 3, N-C 2 H 5 or a group of the general formula CH 2, CH (CH3), CH (C2H5) or C (CH3) 2 and, even more preferably O or CH2, the symbol W ⁷ represents the divalent group of general formula O, S, NH, N [(C 1 -C 4 alkyl)], C = O, S = O or SO2, in particular, the divalent group of general formula O, S, NH or N- [(C1 -C4 alkyl)] and, in particular, O, each of the symbols Q ⁵ and Q ⁶ independently represents hydroxy, uncle, halogen or a group of general formula OR ³⁷ , SR ³⁸ , SM or OM and, in particular, hydroxy, each of the symbols R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ independently represent H, halogen, cyano, nitro, hydroxy, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1-C4) or haloalkoxy (C1- C4) and, in particular, H or alkyl (C1-C4), each of the symbols R ³⁵ and R ³⁶ independently represents hydrogen, alkyl (C1-C4) or haloalkyl (C1-C4) and , in particular, H, methyl or ethyl, the symbols R ³⁷ , R ³⁸ and M have the meanings mentioned above and, preferably, as defined for the compounds of formula (B1) or (B4) above.

58/289 [110] Examples of preferred B ¹ radicals of structural formulas (B5) and (B6) refer to the radicals of structural formulas (B5-1), (B5-2), (B5-3), ( B5-4), (B5-5), (B5-6), (B5-7), (B5-8), (B5-9), (B6-1), (B6-2), (B6- 3):

[111] Compounds (I) are preferred, where B ¹ represents a radical (B7)

R

R (B7) and that the symbols Q ^{r * 7} , R ²¹ and R ²² have the preferred meanings or meanings

59/289 mentioned above and, preferably, the symbol Q ⁷ represents hydroxy, thio, halogen or a group of general formula OR ³⁷ 'SR ³⁸ , SM or OM and, in particular, hydroxy, the symbol R ²¹ represents hydrogen, alkyl (C1-C4), haloalkyl (C1-C4), 5 cycloalkyl (C3-C6), halocycloalkyl (C3-C6) or a C (O) OR ⁵⁴ , C (O) NR ⁵⁵ R ^{56 group} ,

C (O) Het ⁷ , NR ⁵⁷ R ⁵⁸ or Het ⁸ and, in particular, H, alkyl (C-C4), haloalkyl (C-C4) or cycloalkyl (C3-C6), for example, cyclopropyl, the symbol R ²² represents hydrogen, (C1-C4) alkyl, halo (C1-C4), cycloalkyl (C3-C6), halocycloalkyl (C3-C6), alkyl (C1-C4) -thio, alkyl (C1-C4) 10 sulfonyl, (C1 -C4) alkylsulfinyl or a group of the general formula C (O) OR ⁵⁹ , C (O) NR ⁶⁰ R ⁶ \ C (O) Het ⁹ , NR ⁶² R ⁶³ or Het ⁱ⁰ and, in particular, H , (C-C4) alkyl, (C-C4) haloalkyl, (C3-C6) cycloalkyl, (C3-C6) halocycloalkyl, (C-C4) alkylthio, (C-C4) alkylsulfonyl or a group of general formula C (O) OR ⁵⁹ and the symbol R ⁵⁹ represents hydrogen, (C1-C4) alkyl, haloalkyl (C1-C4), cycloalkyl (C3-C6), halocycloalkyl (C3-C6), alkenyl (C2-C4) , haloalkenyl (C2-C4), alkynyl (C2-C4) or the mentioned M group and, preferably, hydrogen, (C-C3) alkyl or the mentioned M group.

[112] Examples of preferred B ⁱ radicals of structural formula (B7) include radicals of structural formulas (B7-1), (B7-2), (B7-3), (B7-4) and (B720 5):

60/289

[113] Compounds (I) are also preferred, where B ¹ represents a radical (B8)

O (B8) and that the symbols R ²³ and R ²⁴ have the preferred meanings or meanings mentioned above and, preferably, the symbol R ²³ represents hydrogen, (C 1 -C 4), haloalkyl (C-C 4), cycloalkyl ( C3-C6), halocycloalkyl (C3-C6), alkoxy (C1-C4) or haloalkoxy (C1-C4), in particular, hydrogen, alkyl (C1-C4), haloalkyl (C1-C4), cycloalkyl (C3-C6) ), (C3-C4) -halocycloalkyl, alkoxy (C1-C4) or haloalkoxy (C1-C4) and, more preferably, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t- butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy or tbutoxy, the symbol R ²⁴ represents hydrogen, halogen, cyano, alkyl (C1-C4), haloalkyl (C1-C4), cycloalkyl (C3-C6), for example, cyclopropyl, alkoxy (C1-C4) or haloalkoxy (C1-C4), in particular hydrogen, alkyl (C1-C3), cyano or cyclopropyl and, more preferably, cyan.

[114] Examples of preferred B ⁱ radicals of structural formula (B8) include radicals of structural formulas (B8-1), (B8-2), (B8-3), (B8-4), (B820 5) and (B8-6):

61/289

O I I O I I O I I ^^ OMe '' oct ^ '' Y ^ O-n-Pr CN CN CN (B8-1) (B8-2) (B8-3) O I I O I I O I I ^ 'Y ^ O-i-Pr ^^ '' Y ^ O-n-Bu O-t-Bu CN CN CN (B8-4) (B8-5) (B8-6)

[115] In structural formulas (B8-1) to (B8-6) and, correspondingly, in other exemplary structural formulas, OMe = methoxy, OEt = ethoxy, On-Pr = n-propoxy, Oi-Pr = isopropoxy, On-Bu = n-butoxy, Oi-Bu = isobutoxy, O-sBu = sec-butoxy and Ot-Bu = tert-butoxy.

[116] The compounds of structural formula (B8) are tautomers of the compounds of structural formulas (B11) and (B12), if Q ⁸ = OH or OM and R ²⁴ = R ³⁰ and R ²³ = R ²⁹ . In particular, when each of the symbols R ²⁴ and R ³⁰ represents CN, in equilibrium, a substantial proportion is described by the tautomer of structural formula (B11).

[117] Compounds (I) are also preferred, in which the symbol B ¹ represents a radical (B9)

O (B9)

The ^ R ² 'in which each of the symbols R ²⁵ and R ²⁶ has, independently of each other, the 15 meanings or preferred meanings mentioned above and, more preferably, each of them represents, independently of each other , hydrogen, (C1-C4) alkyl, halo (C1-C4), alkoxy (C1-C4), haloalkoxy (C1C), alkoxy (C1-C4) -alkyl (C1-C4), haloalkoxy (C1-C4) - (C 1 -C 4) alkyl,

62/289 cycloalkyl (C3-C6), halocycloalkyl (C3-C6), cycloalkoxy (C3-C6), alkenyl (C2-C6), haloalkenyl (C2-C6), alkynyl (C2-C6), haloalkynyl (C2-C6) ), (C1-C4) alkylthio, (C1-C4) alkylsulfonyl, (C1-C4) alkylsulfinyl, NR ⁶⁴ R ⁶⁵ or Het ¹¹ or, more preferably, the symbol R ²⁵ represents hydrogen, alkyl ( C1 -C4), alkoxy (C1-C4), haloalkoxy (C1C4) or cycloalkyl (C3-C6), for example, cyclopropyl, and in particular alkoxy (C1C) and the symbol R ²⁶ represents hydrogen, alkyl (C1-4) C4), alkoxy (C1-C4), haloalkoxy (C1C4) or cycloalkyl (C3-C6), for example, cyclopropyl, and, in particular, alkoxy (C10 C4).

[118] Examples of preferred B ⁱ radicals of structural formula (B9) include radicals of structural formulas (B9-1), (B9-2), (B9-3), (B9-4), (B9- 5), (B9-6), (B9-7), (B9-8) and (B9-9):

0 Y OMe 0 Y ^ OEt θ 'OEt (B9-2) 0 Y O-n-Pr 0 O-n-Pr (B9-3) 0 ^ OMe (B9-1) 0 0 O Y ϊ ÇO-i-Pr ^^ V ^ O-n-Bu Y O-t-Bu 0 O-i-Pr 0 O-n-Bu O-t-Bu (B9-4) (B9-5) (B9-6) O O O Y ϊ ^z OMe Y OEt Y OMe θ ' k O 0¼ (B9-7) (B9-8) (B9-9)

63/289 [119] The compounds of structural formula (B9) are tautomers of the compounds of structural formulas (B13) and (B14), if Q ⁹ = OH or OM and R ²⁵ = R ³¹ and R ²⁶ = R ³² .

[120] Compounds (I) are also preferred, where the symbol B ¹ represents a radical (B10) (B10) and the symbols R ²⁷ and R ²⁸ have the preferred meanings or meanings mentioned above and, preferably, the symbol R ²⁷ represents H, alkyl (C-C4), haloalkyl (C-C4) or cycloalkyl (C3C6), for example, cyclopropyl, the symbol R ²⁸ represents H, alkyl (C-C4), haloalkyl (C-C4) ) or a radical of the general formula C (O) OR ⁶⁶ and the symbol R ⁶⁶ represents hydrogen, (C1-C4) alkyl, haloalkyl (C1-C4), cycloalkyl (C3-C6), halocycloalkyl (C3-C6), alkenyl (C2-C4), haloalkenyl (C2-C4), alkynyl (C2-C4) or the mentioned M group and preferably hydrogen, (C-C3) alkyl or the mentioned M group.

[121] Examples of preferred B ⁱ radicals of structural formula (B10) include radicals of structural formulas (B10-1), (B10-2), (B10-3) and (B10-4):

[122] Compounds (I) are also preferred, where B ⁱ represents a radical (B11)

64/289

Q ⁸

R (B11) in which the symbols Q ⁸ , R ²⁹ and R ³⁰ have the preferred meanings or meanings mentioned above and, preferably, the symbol Q ⁸ represents hydroxy, halogen or a group of general formula OR ³⁷ , SR ³⁸ or OM and, in particular, hydroxy, the symbol R ²⁹ represents H, alkyl (C1-C4), haloalkyl (C1-C4), cycloalkyl (C3Ce), for example, cyclopropyl, alkoxy (C-C4) or haloalkoxy (Ci- C4), the symbol R ³⁰ represents H, halogen, cyano, alkyl (C-C4), haloalkyl (C1-C4), cycloalkyl (C3-C6), for example, cyclopropyl, alkoxy (C-C4) or haloalkoxy (Ci -C4).

[123] Examples of preferred B ⁱ radicals of structural formula (B11) include radicals of structural formulas (B11-1) and (B11-2):

OH I OH I CN CN (B11-1) (B11-2)

[124] Compounds (I) are also preferred, where B ⁱ represents a radical (B13)

O

(B13)

Q “that the symbols Q ⁹ , R ³ⁱ and R ³² have the meanings or preferred meanings mentioned above and, preferably, the symbol Q ⁹ represents hydroxy, halogen or a group of general formula OR ³⁷ , SR ³⁸ or OM and, in particular, hydroxy,

65/289 each of the symbols R ³¹ and R ³² independently represents H, alkyl (C-C4), haloalkyl (C-C4), alkoxy (C-C4), haloalkoxy (C-C4) , (C1 -C4) alkoxy (C-C4) alkyl, (C-C4) haloalkoxy (C-C4) alkyl, (C3-C6) cycloalkyl, (C3-C6) halocycloalkyl, (C3-C6) cycloalkoxy (C3-C6), alkyl ( C1-C4) -thio, (C1-C4) alkylsulfonyl, (C1-C4) alkylsulfinyl, NR ⁶⁴ R ⁶⁵ or Het ⁱ ' ^1, and in particular H, (C1C4) alkyl, haloalkyl (C1-4) C4), alkoxy (C1-C4), haloalkoxy (C1-C4), alkoxy (C1-C4) alkyl (C1-C4), haloalkoxy (C1-C4) -alkyl (C1-C4), cycloalkyl (C3-C6) , halocycloalkyl (C3-C6), cycloalkoxy (C3-C6), alkyl (C-C4) -thio.

[125] Examples of preferred B ⁱ radicals of structural formula (B13) include radicals of structural formulas (B13-1), (B13-2), (B13-3), (B13-4), (B13 -5), (B13-6), (B13-7), (B13-8) and (B13-9):

oh Y ^ OMe θ 'OMe OH ^^ V ^ OEt O ^ OEt (B13-2) OH ^^^ O-n-Pr O ^ ^ O-n-Pr (B13-3) (B13-1) OH OH OH ^ Ό-ι-Pr O-n-Bu <^ O-t-Bu O O-i-Pr O-n-Bu O , r-i O-t-Bu (B13-4) (B13-5) (B13-6) O O O r | OMe I read ^Et X Ϊ '| OMe HO ^ HO ^ HO (B13-7) (B13-8) (B13-9)

[126] Compounds (I) are also preferred, in which L represents a radical of structural formula

66/289

B ² the symbol A ² represents a radical of the structural formulas (A1) to (A12) mentioned, the symbol B ² represents hydroxy, thio, halogen or a group of general formula 5 OR ³³ , OM, SR ³⁴ , SM or -NR ^B R ^C and, preferably, hydroxy, halogen or a group of general formula OR ³³ , OM, SR ³⁴ or -NR ^B R ^C , the symbols R ^B and R ^C , independently of each other, have the defined meanings before and preferably independently represent hydrogen, hydroxy, alkoxy (C1-C4), alkyl (C1-C4), haloalkyl (C1-C4), phenyl which is unsubstituted or is substituted with a or more radicals selected from the group consisting of halogen, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1-C4), haloalkoxy (C1-C4), or benzyl that is unsubstituted in the phenyl residue or is substituted with one or more radicals selected from the group consisting of halogen, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1-C4), haloalkoxy (C1-C4) or -NR * R **, in what and each of the symbols R *, R ** independently represents H, alkyl (C-C4), alkenyl (C2-C4), alkynyl (C2-C4), alkoxy (C-C4) - alkyl (C1-C4), alkanoyl (C1-C4), [haloalkyl (C1-C4)] - carbonyl, [alkoxy (C1-C4)] - carbonyl, [haloalkoxy (C1-C4)] - carbonyl, cycloalkyl (C3 -C6), cycloalkyl (C3-Ce) -alkyl (Ci20 C4), phenyl, phenyl-alkyl (Ci-C4), where each of these last 4 radicals is unsubstituted in the cycle or is substituted with one or more selected radicals between the set consisting of halogen, alkyl (C-C4), haloalkyl (C1-C4), alkoxy (C1-C4) or haloalkoxy (C1-C4) or, in the case of cycloalkyl, also with oxo, or the symbols R * and R **, together with the nitrogen atom, represent a 3- to 6-membered heterocycle preferably saturated, which, in addition to the nitrogen atom, may contain one or two other hetero atoms in the ring of the set consisting of N, O and S and which can be unsubstituted or replaced with one or more roots is selected from the set

67/289 by alkyl (C1-C4), haloalkyl (C1-C4) and oxo or, in particular, the symbol R ^B represents hydrogen, hydroxy, alkoxy (C1-C4), alkyl (C1-C4), phenyl, benzyl or -NR * R **, where each of the symbols R *, R ** independently represents H or alkyl (C1-C4) and the symbol R ^C represents hydrogen, alkyl (C1-C4) ), phenyl or benzyl or the group -NR ^B R ^C represents a radical of the general formula -NH2, -NHOH, NHOCH3, -NHCH3, -N (CH3) 2, -NH-NH2 or -NH-N (CH3) 2 , the symbols (R ⁱ ) m, (R ² ) n, R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ⁱ⁰ , R, R ⁱ² , R ⁱ³ , R ⁱ⁴ , R ⁱ⁵ , R ⁱ⁶ , R ⁱ⁷ , R ⁱ⁸ , R ⁱ⁹ , R ²⁰ , R ^{2 1} , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ²⁶ have the preferred meanings or meanings mentioned above, each of the symbols W ⁱ and W ⁶ independently represent the divalent oxygen, sulfur group or a group of the general formula NH, N [(C 1 -C 4 alkyl)], C = O, S = O, SO2 or CR ³⁵ R ³⁶ , each of the symbols W ² , W ³ , W ⁴ , W ⁵ and W ⁷ represents, d and independently of each other, the divalent group of general formula O, S, NH, N- [(C 1 -C4 alkyl)], C = O, S = O or SO2, the symbols R ³³ , R ³⁴ and M have the meanings or preferred meanings mentioned above, and preferably each of the symbols R ³³ and R ³⁴ independently represents (C 1 -C 4) alkyl, C 1 -C haloalkyl, C 1 -C 4 alkoxy -alkyl (C1-C4), cycloalkyl (C3C6) which is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, alkyl (C1-C4) and alkoxy (C1-C4), phenyl which is not substituted or substituted with one or more radicals selected from the group consisting of halogen, cyano, hydroxy, nitro, alkyl (C1-C4), haloalkyl (C1-C4) and alkoxy (C1-C4), or a group of general formula -C (O) R ⁶⁷ , C (O) OR ⁶⁸ , -C (O) NR ⁶⁹ R ⁷⁰ , -C (O) Het ⁱ² or -SO2R ^{7 1} , in particular, each of the symbols R ³³ and R ³⁴ independently represents alkyl (C1-C6), haloalkyl (C1-C4), c icloalkyl (C3-C6), halocycloalkyl (C3-C6), phenyl which is unsubstituted or is substituted with one or

68/289 plus radicals selected from the group consisting of halogen and (C 1 -C 4) alkyl, or a group of general formula -C (O) R ⁶⁷ , -C (O) OR ⁶⁸ , C (O) NR ⁶⁹ R ⁷⁰ , -C (O) Het ¹² or -SO2R ⁷¹ , each of the symbols R ³⁵ and R ³⁶ has, independently of each other, the meaning defined for R ³ or preferably represents and independently of each other, H, (C1-C4) alkyl or (C1-C4) haloalkyl, in particular, H or (C1-C2) -alkyl and, in particular, H, methyl or ethyl, the symbol R ⁶⁷ represents hydrogen, (C1-6) alkyl C6), haloalkyl (C1-4), phenyl or benzyl, in which each of these last 2 radicals, independently of each other, is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, cyano , (C1 -C4) alkyl and halo (C1C4) and, in particular, H or alkyl (C1-C4), R ⁶⁸ represents alkyl (C1-C6) or haloalkyl (C1-C4) and, in particular, alkyl (Ci-C4), each of the symbols R ⁶⁹ and R ⁷⁰ represents, in a way i independent of each other, hydrogen, alkyl (C-C4), benzyl, cycloalkyl (C3-C6) or phenyl, in which each of these last 2 radicals, independently of each other, is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, nitro, cyano, alkyl (C1-C4) and haloalkyl (C1-C4) or each of them, in particular and independently, from each other, H or alkyl (C1-C3) , the symbol R ^{7 1} represents alkyl (C 1 -C 4), haloalkyl (C 1 -C 4), phenyl or benzyl, in which each of these last 2 radicals, independently of each other, is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, cyano, alkyl (C-C4), alkenyl (C2-C4) and haloalkyl (C1-C4) and, in particular, alkyl (C1-C4), haloalkyl (C1-C4) , benzyl or phenyl that is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, alkyl (C1-C4) and haloalkyl (C1-C4), the same Het ⁱ² cake represents a saturated or partially unsaturated radical of

69/289 a heterocycle that has 3 to 6 ring atoms and at least one nitrogen atom as the ring heteroatom in position 1 of the ring and, optionally,

1,2 or 3 other ring hetero atoms of the set consisting of N, O and S, where the radical of the heterocycle in the nitrogen atom at position 1 of the ring is attached to the remainder of the molecule of the compound of formula (I) and wherein the heterocycle is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1-C4), haloalkoxy (C1-C4) , (C1 -C4) alkylthio and oxo, in particular, is unsubstituted or substituted with one or more radicals selected from the group consisting of (C1-C4) alkyl and (C1-C4) haloalkyl and, in particular, one morpholino, piperidine or pyrrolidine group.

[127] Compounds (I) are also preferred, in which the symbol A ² represents a radical of the structural formulas (A1) to (A12) mentioned, each of the symbols R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ⁱ⁰ , R, R ⁱ² , R ⁱ³ , R ⁱ⁴ , R ⁱ⁵ , R ⁱ⁶ , R ⁱ⁷ , R ⁱ⁸ , R ⁱ⁹ and R ²⁰ represent, independently of each other, H, halogen, cyano, nitro, hydroxy, alkyl (C1-C4), haloalkyl (C1-C4), cycloalkyl (C3-C6), alkoxy (C1-C4) or haloalkoxy (C1-C4) and, in particular, H or alkyl (Ci-C4), or the symbols R ³ and R ⁵ in the group of structural formula (A1), together, represent a divalent bridge as defined above, the symbol R ^{2 1} represents H, alkyl (Ci-C4), haloalkyl (C1-C4), cycloalkyl (C3C6), halocycloalkyl (C3-C6) or a group C (O) OR ⁵⁴ , C (O) NR ⁵⁵ R ⁵⁶ , C (O) Het ⁷ , NR ⁵⁷ R ⁵⁸ or Het ⁸ and preferably (C1-C4) alkyl, haloalkyl (C1-C4), cycloalkyl (C3-C6) or a C (O) OR ^{54 group} , the symbol R ²² represents H, (C1-C4) alkyl, haloalkyl (C1-C4), cycloalkyl (C3C6), halocycloalkyl a (C3-C6), (C1-C4) alkylthio, (C1-C4) alkylsulfonyl or a group of the general formula C (O) OR ⁵⁹ , C (O) NR ⁶⁰ R ⁶ⁱ , C (O) Het ⁹ , NR ⁶² R ⁶³ or Het ⁱ⁰ and preferably (C1-C4) alkyl, haloalkyl (C1-C4), cycloalkyl (C3-C6), alkyl (C1-C4) sulfonyl or a C (O) group OR ⁵⁹ , the symbol R ²³ represents H, alkyl (C1-C4), haloalkyl (C1-C4), cycloalkyl (C370 / 289

Ce), halocycloalkyl (C3-C6), alkoxy (C1-C4) or haloalkoxy (C1-C4) and preferably H, alkyl (C1-C4), haloalkyl (C1-C4), cycloalkyl (C3-C6) , for example, cyclopropyl, alkoxy (C1-C4) or haloalkoxy (C1-C2), the symbol R ²⁴ represents H, halogen, cyano, alkyl (C1-C4), haloalkyl (C1-C4), cycloalkyl (C3-C6 ), alkoxy (C1-C4) or haloalkoxy (C1-C4) and preferably H, halogen, cyano, alkyl (C1-C4), haloalkyl (C1-C4), cycloalkyl (C3-C6), for example, cyclopropyl, alkoxy (C1-C4) or haloalkoxy (C1-C2), each of the symbols R ²⁵ and R ²⁶ independently represents H, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1-C4), haloalkoxy (C1-C4), alkoxy (C1C4) -alkyl (C1-C4), haloalkoxy (C1-C4) -alkyl (C1-C4), cycloalkyl (C3-C6), cycloalkoxy (C3) -C6), alkenyl (C2-C6), alkynyl (C2-C6), alkyl (C1-C4) -thio, alkyl (C1-C4) sulfonyl, NR ⁶⁴ R ⁶⁵ or Het ' ¹ ' ¹ and, preferably, H, alkyl (C1-C4), haloalkyl (C1 -C4), alkoxy (C1-C4), haloalkoxy (C1-C4), alkoxy (C1-C2) -alkyl (C1-C2), haloalk xi (C1 -C2) -alkyl (C1-C2) or cycloalkyl (C3-C6), for example, cyclopropyl, each of the symbols R ⁵⁴ and R ⁵⁹ independently represents H, alkyl (C1-C4) , haloalkyl (C1-C4), cycloalkyl (C3-C6), alkenyl (C2-C4), alkynyl (C2-C4) or the mentioned M group, each of the symbols R ⁵⁵ , R ⁵⁶ , R ⁵⁷ , R ⁵⁸ , R ⁶⁰ , R ⁶ ', R ⁶² , R ⁶³ , R ⁶⁴ and R ⁶⁵ independently represent H, alkyl (C 1 -C 4) which is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, nitro, cyano, and phenyl which is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, nitro, cyano, alkyl (C1-C4) and haloalkyl (C1-C4), or cycloalkyl (C3-C6) which is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, alkyl (C-C4) and haloalkyl (Ci-C4), or phenyl which is unsubstituted or is substituted with one or more radicals selected from the group consisting of halogen, nitro, cyano, alkyl (CiC4) and haloalkyl (Ci-C4), each of the symbols Het ⁷ , Het ⁸ , Het ⁹ , Het ⁱ⁰ and Het ' ¹ ' ¹ represents , in a way

71/289 independent of each other, a saturated or partially unsaturated radical of a heterocycle that has 3 to 6 ring atoms and at least one nitrogen atom as the ring heteroatom in position 1 of the ring and, optionally,

1,2 or 3 other ring hetero atoms of the set consisting of N, O and S, where the radical of the heterocycle in the nitrogen atom at position 1 of the ring is attached to the remainder of the molecule of the compound of formula (I) and wherein the heterocycle is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1-C4), haloalkoxy (C1-C4) , (C1 -C4) alkylthio and oxo, in particular, is unsubstituted or substituted with one or more radicals selected from the group consisting of (C1-C4) alkyl and (C1-C4) haloalkyl, and in particular , a morpholino, piperidine or pyrrolidine group.

[128] Here, compounds (I) are preferred, where A ² represents one of the radicals (A1) to (A12) and B ² represents hydroxy, thio, halogen or a group of general formula OR ³³ , SR ³⁴ , SM or OM, in particular hydroxy, halogen or a group of general formula OR ³³ , SR ³⁴ or OM and, more preferably, hydroxy, the symbols R ³³ , R ³⁴ and M have the mentioned meanings or preferred meanings before and preferably each of the symbols R ³³ and R ³⁴ independently represents alkyl (C1-Ce), haloalkyl (C1-C6), alkoxy (C1-C4) -alkyl (C1-C4) ), cycloalkyl (C3Ce) which is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, alkyl (C-C4) and alkoxy (C-C4), phenyl which is unsubstituted or is substituted with a or more radicals selected from the group consisting of halogen, cyano, hydroxy, nitro, alkyl (C1-C4), haloalkyl (C1-C4) and alkoxy (C1-C4), or a group of general formula -C ( O) R ⁶⁷ , C (O) OR ⁶⁸ , -C (O) NR ⁶⁹ R ⁷⁰ , -C (O) Het ⁱ² or -SO2R ⁷ i in particular, each of the symbols R ³⁷ and R ³⁸ represents, in a independently of one another, alkyl (C-C6), haloalkyl (C-C4), cycloalkyl (C3-C6), halocycloalkyl (C3-C6), phenyl which is unsubstituted or substituted with one or

72/289 plus radicals selected from the group consisting of halogen and (C 1 -C 4) alkyl, or a group of general formula -C (O) R ⁶⁷ , -C (O) OR ⁶⁸ , C (O) NR ⁶⁹ R ⁷⁰ , -C (O) Het ¹² or -SO2R ⁷¹ , and, more preferably, each of the symbols R ³⁷ and R ³⁸ independently represents (C 1 -C 4) alkyl, phenyl which is unsubstituted or is substituted with one or more radicals selected from the group consisting of halogen and (C 1 -C 4) alkyl, or a group of general formula -C (O) R ⁶⁷ , C (O) OR ⁶⁸ or -SO2R ⁷¹ , the symbol R ⁶⁷ represents hydrogen, alkyl (C1-C6), haloalkyl (C1-C4), phenyl or benzyl, in which each of these last 2 radicals, independently of each other, is unsubstituted or substituted with one or more radicals selected from among the group consisting of halogen, cyano, alkyl (C1-C4) and haloalkyl (C1C4) and, in particular, H or alkyl (C1-C4), for example, H, methyl, ethyl, n-propyl, isopropyl, n- butyl, sec-butyl, isobutyl or t-butyl, the symbol R ⁶⁸ represents alkyl (C 1 -C 6) or haloalkyl (C 1 -C 4) and, in particular, alkyl (C 1 -C 4), each of the symbols R ⁶⁹ and R ⁷⁰ independently represents between si, hydrogen, alkyl (C-C4), benzyl, cycloalkyl (C3-C6) or phenyl, in which each of these last 2 radicals, independently of each other, is unsubstituted or is substituted with one or more selected radicals between the group consisting of halogen, nitro, cyano, alkyl (C1-C4) and haloalkyl (C1-C4) or, in particular, each of them independently represents H or alkyl (C1-C3), R ^{7 1} represents alkyl (C 1 -C 4), haloalkyl (C 1 -C 4), phenyl or benzyl, in which each of these last 2 radicals, independently of each other, is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, cyano, alkyl (C-C4), alkenyl (C2-C4) and haloalkyl (Ci-C4) and, in particular, alkyl (Ci-C4), haloalkyl (Ci-C 4), benzyl or phenyl that is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, (C-C4) alkyl and

73/289 haloalkyl (C1-C4), the symbol Het ¹² represents a morpholino, piperidine or pyrrolidine group and the symbol M represents an equivalent of a cation, preferably an equivalent of a metal ion, an ammonium ion that is optionally substituted with 1 to 4 radicals, the same or different, selected from the group consisting of alkyl (C-C4), cycloalkyl (C3-C6), phenyl, cycloalkyl (C3Ce) -alkyl (C1-C4) and phenyl-alkyl (C1-C4) ) and, in particular, (C1-C4) alkyl, or a tertiary sulfonium ion that is preferably substituted with 3 radicals, the same or different, selected from the group consisting of alkyl (C1-C4), cycloalkyl (C3-C6), phenyl, cycloalkyl (C3-C6) -alkyl (C1-C4) and phenyl-alkyl (C1-C4) and, in particular, alkyl (C1-C4).

[129] In this case, compounds (I) are preferred, where A ² represents a radical (A1)

whereas the symbols W ⁱ , R ³ , R ⁴ , R ⁵ and R ⁶ have the preferred meanings or meanings mentioned above, and preferably the symbol W ⁱ represents the divalent group of general formula O, S, NH, N [ (C1 -C4) alkyl], C = O, S = O, SO2 or CR ³⁵ R ³⁶ and, in particular, the divalent group of general formula O, S, C = O or CR ³⁵ R ³⁶ , where each of the symbols R ³⁵ and R ³⁶ represents, independently of each other, hydrogen, alkyl (C 1 -C 4) or haloalkyl (C 1 -C 4), in particular, the symbol W ⁱ represents the divalent group C (O), CH 2, CH (CH3) or C (CH3) 2, each of the symbols R ³ , R ⁴ , R ⁵ and R ⁶ independently represents H, halogen, cyano, nitro, hydroxy, (C 1 -C 4) ), haloalkyl (C1-C4), alkoxy (C1-C4) or haloalkoxy (C1-C4) and, in particular, H or alkyl (C1-C4) or

74/289 the symbols R ³ and R ⁵ together represent a divalent bridge of general formula -CH2CH2-, -CH2CH2CH2-, -CH (CH3) CH2-, -C (CH3) 2CH2-, CH2CH (CH3) - , -CH2C (CH3) 2-, -C (CH3) CH (CH3) -, -CH2CH2CH2-, -CH = CH-, -CH = CHCH2-, -CH2CH = CH-, -OCH2-, -CH2O-, -OCH2CH2-, -CH2OCH2-, 5 CH2CH2O- or -OCH2O- and, in particular, of the general formula -CH2CH2- or -CH = CH [130] As examples of preferred A ² radicals of structural formula (A1) the radicals of structural formulas (A1-1) to (A1-9):

C-C, such as (A1-3) and (A1-4), then the corresponding double bonded isomers covered by structural formula (A1) are also preferred.

[132] Compounds (I) are also preferred, where the symbol A ² represents a radical (A5)

75/289

(A5) in which the symbols W ⁴ , W ⁵ , R ¹⁵ and R ¹⁶ have the meanings or preferred meanings mentioned above and, preferably, each of the symbols W ⁴ and W ⁵ represents, independently of each other, the divalent group of the general formula O, S, NH, N- [(C1 -C4 alkyl)], C = O, S = O or SO2, in particular the divalent group of the general formula O or S and, in particular, Each of the symbols R ¹⁵ and R ¹⁶ independently represents H, halogen, cyano, nitro, hydroxy, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1C4) or haloalkoxy (C1-C4) and, in particular, hydrogen or alkyl (C1-C4).

[133] An example of preferred A ² radicals of structural formula (A5) is the radical of structural formula (A5-1):

(A5-1) [134] Compounds (I) are also preferred, in which the symbol A ² represents a radical (A6) or (A7) w

(A7) and that the symbols W ⁶ , W ⁷ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ have the preferred meanings or meanings mentioned above and, preferably,

76/289 the symbol W ⁶ represents the divalent group of general formula O, S, NH, N [(C 1 -C 4 alkyl)], C = O, S = O, SO2 or CR ³⁵ R ³⁶ , in particular, the group divalent of general formula O, S, NH, N- [(C 1 -C 4 alkyl)] or a group of general formula CR ³⁵ R ³⁶ , more preferably O, NH, N-CH 3, N-C 2 H 5 or a group of formula general

CH2, CH (CH3), CH (C2H5) or C (CH3) 2 and, even more preferably, O or CH2, in which each of the symbols R ³⁵ and R ³⁶ independently represents hydrogen, alkyl (C1-C4) or haloalkyl (C1-C4), in particular, the symbol W ⁶ represents the divalent group CH2, CH (CH3) or C (CH3) 2, the symbol W ⁷ represents the divalent group of general formula O, S, NH, N [(C 1 -C 4 alkyl)], C = O, S = O or SO 2, in particular, the divalent group of the general formula O, S, NH or N- [(C 1 -C 4 alkyl)] and , in particular, O and each of the symbols R ⁱ⁷ , R ⁱ⁸ , R ⁱ⁹ and R ²⁰ independently represent H, halogen, cyano, nitro, hydroxy, (C1-C4) alkyl, haloalkyl (Ci -C4), alkoxy (C1-C4) or haloalkoxy (C1-C4) and, in particular, H or alkyl (C1-C4).

[135] Examples of preferred A ² radicals of structural formula (A6) include radicals of structural formulas (A6-1) to (A6-11):

77/289

[136] As preferred A ² radicals of structural formula (A7) are the corresponding radicals of structural formulas (A7-4) to (A7-11) (structural formulas not shown), which represent double bond isomers in terms of the double bond presented as an arrow from the radicals of structural formulas (A6-4) to (A6-11).

[137] In the case of radicals (A6) substituted asymmetrically at the C-C double bond, such as (A6-2) and (A6-3), then the corresponding double bond isomers covered by structural formula (A6) are also preferred.

[138] Compounds (I) are also preferred, in which the symbol A ² represents a radical (A8) or (A9)

and that the symbols R ²¹ and R ²² have the meanings or preferred meanings mentioned above, and preferably the symbol R ²¹ represents hydrogen, (C 1 -C 4) alkyl, halo (C 1 -C 4) alkyl,

78/289 cycloalkyl (C3-C6), halocycloalkyl (C3-C6) or a C (O) OR ⁵⁴ , C (O) NR ⁵⁵ R ⁵⁶ , C (O) Het ⁷ , NR ⁵⁷ R ⁵⁸ or Het ^{8 group} , in particular H, alkyl (C1-C4), haloalkyl (C1-C4) or cycloalkyl (C3-C6), for example, cyclopropyl, and R ²² represents hydrogen, alkyl (C1-C4), haloalkyl (Ci -C4), 5 (C3-C6) cycloalkyl, (C3-C6) halocycloalkyl, (C-C4) alkylthio, (C-C4) alkyl sulfonyl, (C-C4) alkylsulfinyl or a group of general formula C (O) OR ⁵⁹ ,

C (O) NR ⁶⁰ R ⁶ \ C (O) Het ⁹ , NR ⁶² R ⁶³ or Het ⁱ⁰ and, in particular, H, (C-C4) alkyl, halo (C-C4) alkyl, cycloalkyl (C3-C6) , halocycloalkyl (C3-C6), alkyl (C1-C4) -thio or alkyl (C1-C4) -sulfonyl.

[139] Examples of preferred A ² radicals of structural formula (A8) include radicals of structural formulas (A8-1) to (A8-5):

.. (A8-1) (A8-2) (A8-3) THE (A8-4) M · (A8-5)

[140] Preferred A ² radicals of structural formula (A9) refer to the corresponding radicals of structural formulas (A9-1) to (A9-5) (structural formulas not shown) representing double bonded isomers with respect to regarding the double bond presented as an arrow of the radicals of structural formulas (A8-1) to (A8-5).

[141] Compounds (I) are also preferred, where the symbol A ² represents a radical (A10) or (A11)

79/289

R ²³ ^^ O (A10) (A11) wherein R ²³ represents H, alkyl (C 1 -C 4), haloalkyl (C 1 -C 4), cycloalkyl (C 3 Ce), for example, cyclopropyl, alkoxy (C-C 4) or halo (C 1 -C 4) alkoxy and, more preferably, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy or tbutoxy and the symbol R ²⁴ represents H, halogen, cyano, alkyl (C-C4), haloalkyl (C-C4), cycloalkyl (C3-C6), for example, cyclopropyl, alkoxy (C-C4) ) or halo (C 1 -C 4) alkoxy, in particular hydrogen, (C 1 -C 3) alkyl, cyano or cyclopropyl and, more preferably, cyan.

[142] Examples of preferred A ² radicals of structural formula (A10) include radicals of structural formulas (A10-1), (A10-2), (A10-3), (A10-4), (A10 -5), (A10-6), (A10-7), (A10-8) and (A10-9):

O AA O aa O THE, / CN CN CN (A10-1) (A10-2) (A10-3) O II O II O I ^ AoMe ^ '' OEt ^ yO-n-Pr CN CN CN (A10-4) (A10-5) (A10-6)

80/289

O II O II 0 II ^ yO-i-Pr ^ γΌ-n-Bu ^ y ^ O-t-Bu CN CN CN (A10-7) (A10-8) (A10-9)

[143] As preferred A ² radicals of structural formula (A11) are the corresponding radicals of structural formulas (A11-1) to (A11-9) (structural formulas not shown) which represent the double bond isomers with respect to regarding the double bond presented as an arrow of the radicals 5 of structural formulas (A10-1) to (A10-9).

[144] Compounds (I) are also preferred, where the symbol A ² represents a radical (A12)

O

The ² 'r ²² (A12) and that each of the symbols R ²⁵ and R ²⁶ independently represents H, alkyl (C 1 -C 4), haloalkyl (C 1 -C 4), alkoxy (C 1 -C 4) , halo (C1-C4), alkoxy (C1 -C4) -alkyl (C1-C4), haloalkoxy (C1-C4) -alkyl (C1-C4), cycloalkyl (C3-C6), halocycloalkyl (C3-C6), cycloalkoxy ( C3-C6), (C1-C4) alkylthio, (C1-C4) alkyl sulfonyl, (C1-C4) alkylsulfinyl, NR ⁶⁴ R ⁶⁵ or Het ' ¹ ' ¹ and, in particular, H, alkyl ( C15 C4), haloalkyl (C1-C4), alkoxy (C1-C4), haloalkoxy (C1-C4), alkoxy (C1-C4) alkyl (C1-C4), haloalkoxy (C1-C4) -alkyl (C1-C4) ), cycloalkyl (C3-C6), halocycloalkyl (C3-C6), cycloalkoxy (C3-C6), alkyl (C-C4) -thio.

[145] Examples of preferred A ² radicals of structural formula (A12) include radicals of structural formulas (A12-1) to (A12-9):

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double C-C, such as (A12-7), (A12-8) and (A12-9), then the corresponding double bond isomers covered by structural formula (A12) are also preferred.

[147] The compounds of formula (I) according to the invention include all stereoisomers that may occur based on centers of asymmetry or double bonds in the molecule, the configuration of which is not specifically shown in the structural formula or which are not specified explicitly, and mixtures thereof, including racemic compounds and mixtures partially enriched with particular stereoisomers.

[148] The invention also includes all tautomers, such as keto and enol tautomers, and their mixtures and salts, if suitable functional groups are present.

[149] The present invention also provides processes for the preparation of compounds of formula (I) and / or their salts. This comprises processes that can be carried out in a manner analogous to known methods.

[150] (a) By way of example, compounds of formula (I) and their salts, in which L represents a radical of formula C (= A ¹ ) -B ¹ , B ¹ represents a radical of structural formulas (B1) to (B9) and (B11) to (B14) and each of the symbols Q ¹ to Q ⁹ represents OH, SH, SM or OM and the other radicals have the meanings defined in the respective formula compound structural (I) to be prepared, are obtained according to a process [variant (a)], characterized by the fact that a compound of structural formula (II) is directly reacted

where the symbols A ¹ , (R ¹ ) m and (R ² ) n have the meanings defined in structural formula (I) and the symbol Y represents a leaving group, preferably a halogen atom and, in particular, an atom of chlorine, with a compound of the general formula HB ¹ , in which the symbol B ¹ has the meaning defined in the radical L and each of the symbols Q ¹ to Q ⁹ has the meanings defined in the compound of structural formula (I) to be prepared , to obtain the compound (I), or to obtain the product of O- or Salkylation as an intermediate, the intermediate of O- or S-alkylation thus formed undergoing rearrangement to obtain the compound of structural formula (I) as a C-alkylation product [see scheme below, where the reagent of general formula (H-B1 *) is used as an example for compound HB ¹ ].

83/289 [151] According to variant (a), the reagents preferably used are compounds of general formula HB ¹ and compounds of structural formula (I) are prepared, in which each of the symbols Q ¹ to Q ⁹ in the group B ¹ represents the radical OH or OM.

[152] C-C acylations can be carried out in a manner analogous to known processes, such as catalyzed reactions based on one or more steps.

[153] Analogous one-step processes using bases, such as calcium hydroxide, are known, for example, from B. S. Jensen, Acta Chem. Scand. 1959, Vol. 13, p.1668 (see diagram below for the preparation of the compound (I-A)).

[154] Analogous one-step processes using bases, such as sodium hydride, are described, for example, by Mulrooney et al., J. Org. Chem. 75, 2010, 16, and by Yadav et al. Chem. Lett. 39, 2010, 280. For example, the reaction can be carried out in a suitable polar aprotic organic solvent, such as dimethylformamide or tetrahydrofuran, at a temperature between 0 ° C and 120 ° C.

[155] Analogous one-step processes using organic bases, such as triethylamine, in the presence of Lewis acids, such as magnesium chloride, are described, for example, by Little et al., J. Org. Chem. 65, 2000, 8096. For example, the reaction can be carried out in a suitable organic aprotic solvent, such as dichloromethane, at a temperature between 0 ° C and 120 ° C.

[156] The analogous two-step processes, in which the base-catalyzed O-acylation reaction is carried out and then rearranged, are known, for example, from EP-A-0186117, WO 2008/125213, WO 2011/012248; EP 0625 505 and literature cited therein; see the diagram below in which the preparation of compound (IA) using the O-alkylation product (I-Zw) is used, as an example, where compound (IA) corresponds to compound (I), where the symbol B ¹ represents a radical of structural formula (B1) and the symbol Q ¹ represents an OH radical.

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Scheme

(II) +

(R ² ) in

HO

R

R R

O

O

R

R R '(H-B1 *)

O

R

R (I-Zw) (I-A) [157] The process involving rearrangement of the compound (I-Zw) or similar intermediates is optionally carried out using a rearrangement reagent. For this purpose, suitable chemicals are used for rearrangements, for example, the reagents of trimethylsilyl cyanide, potassium cyanide and cyanohydrin acetone, known from analogous reactions.

[158] The rearrangement process for the preparation of compounds of formula (I) is preferably carried out using one or more diluents. Suitable diluents include, in particular, organic solvents which are inert under the reaction conditions. These comprise, in particular, aliphatic, alicyclic or aromatic hydrocarbons optionally

Halogenated 85/289, such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether; ketones, such as acetone, butanone or methyl isobutyl ketone; nitriles, such as acetonitrile, propionitrile or butyronitrile; amides, such as N, Ndimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; esters, such as methyl acetate or ethyl acetate; sulfoxides, such as dimethyl sulfoxide.

[159] When carrying out the rearrangement process, the reaction temperatures can vary over a relatively wide range. In general, the process is carried out at a temperature between 0 ° C and 150 ° C and preferably between 10 ° C and 120 ° C. In general, the rearrangement is carried out at atmospheric pressure. However, it is also possible to carry out the process under reduced pressure under high pressure or under reduced pressure - generally between 0.1 bar and 10 bar.

[160] In the process mentioned above and in the following processes, in some cases, solvents are used. In this context, the term "inert solvents" means, in each case, solvents that are inert under the particular reaction conditions, but that do not have to be inert under any reaction conditions.

[161] The process described in each case can be carried out in apparatus normally present in the laboratory, in pilot installations and in industrial installations, for the preparation of commercial quantities and industrial processes or, alternatively, also in a microwave oven.

[162] (b) The compounds of structural formula (I), and their salts, in which L represents a radical of structural formula -C (= A ¹ ) -B ¹ , B ¹ represents a radical of formulas structural (B1) to (B7) and (B11) to (B14) and each of the symbols Q ¹ to Q ⁹ , in group B ¹ , represents a group of general formula SH or SM and the other radicals have the meanings defined as as in the respective compound of structural formula (I) to be prepared, are

86/289 obtained, for example, by means of a process [variant (b)], characterized by the fact that a compound of structural formula (I) is reacted, in which the symbol L represents a radical of structural formula -C ( = A ¹ ) -B ¹ , where the symbol A ¹ has the meaning defined in structural formula (I) and the symbol B ¹ has a meaning defined in a similar way to the radical B ¹ in structural formula (I), with the with the exception of each of the symbols Q ¹ to Q ⁹ , in group B ¹ , represent the group OH or OM, with a halogenating agent, preferably a carbonyl halide, for example, with oxalyl chloride (Cl-CO-CO -Cl), to obtain the compound (I), in which each of the symbols Q ¹ to Q ⁹ , in group B ¹ , represents an ambient temperature of halogen, preferably a chlorine atom, with a sulfurizing agent, preferably a sulphide, for example, disodium sulphide, and optionally removing or isolating the desired compound of structural formula (I) from the mixture the reaction. Such methods are known to those skilled in the art and are described, for example, in Journal of Heterocyclic Chemistry, 25 (3), 901-6; 1988, for nucleophilic substitution with Na2S.

[163] For example, the reaction can also be carried out in an aprotic organic solvent, such as tetrahydrofuran, if appropriate under heating to reflux; see, EP 249150.

[164] (c) The compounds of structural formula (I), and their salts, in which L represents a radical of structural formula -C (= A ¹ ) -B ¹ , B ¹ represents a radical of formulas structural (B1) to (B7) and (B11) to (B14) and each of the symbols Q ¹ to Q ⁹ , in group B ¹ , represents a group of general formula OR ³⁷ and the other radicals have the meanings as defined in the respective compound of structural formula (I) to be prepared, they are obtained, for example, by means of a process [variant (c)], characterized by the fact that a compound of structural formula (I) is reacted, in which the symbol L represents a radical of structural formula -C (= A ¹ ) -B ¹ , where the symbol A ¹ has the meaning defined in the structural formula (I) and the symbol B ¹ has the meaning defined in a similar way to radical B ¹ in structural formula (I),

87/289 with the exception of each of the symbols Q ¹ to Q ⁹ , in group B ¹ , represent the group OH or OM, with a compound (alkylating, acylating or arylating agent) of the general formula Y'-R ³⁷ , wherein Y 'represents a leaving group, and the desired compound of formula (I) is optionally removed from the reaction mixture or isolated. Such methods are known, in principle, to those skilled in the art and are described, for example, in DOS 2513750 (= DE 2513750).

[165] In this case, the reaction according to variant (c) can be carried out using bases, preferably amine bases, such as triethylamine, for example, in a suitable aprotic organic solvent, such as dichloromethane, preferably at a temperature between 0 ° C and 25 ° C; see, WO 2009115788.

[166] (d) The compounds of structural formula (I), and their salts, in which L represents a radical of structural formula -C (= A ¹ ) -B ¹ , B ¹ represents a radical of formulas structural (B1) to (B7) and (B11) to (B14) and each of the symbols Q ¹ to Q ⁹ , in group B ¹ , represents a group of general formula SR ³⁸ and the other radicals have the meanings as defined in the respective compound of structural formula (I) to be prepared, they are obtained, for example, by means of a process [variant (d)], characterized by the fact that a compound of structural formula (I) is reacted, in which the symbol L represents a radical of the general formula -C (= A ¹ ) -B ¹ , where the symbol A ¹ has the meaning defined in the structural formula (I) and the symbol B has the meaning defined in a manner analogous to the radical B ¹ in structural formula (I), with the exception of each of the symbols Q ¹ to Q ⁹ , in group B ¹ , represent the group SH or SM, with a compound (alkylating agent, acylation or arylation) of general formula Y'R ³⁸ , wherein Y 'represents a leaving group, and the desired compound of structural formula (I) is optionally from the reaction mixture or isolate. Such methods are known in principle to those skilled in the art. Reactions in the presence of suitable inorganic or organic bases, such as potassium carbonate or potassium tert-88/289 butoxide, in solvents such as tetrahydrofuran are preferred at a temperature between 0 ° C to 80 ° C; according to WO 2008113089.

[167] (e) The compounds of structural formula (I), and their salts, in which the symbol L represents a radical of structural formula -C (= A ¹ ) -B ¹ , the symbol B ¹ represents a radical of formulas structural (B1) to (B7) and (B11) to (B14) and each of the symbols Q ¹ to Q ⁹ , in group B ¹ , represents a group of general formula SR ³⁸ and the other radicals have the meanings as defined in the respective compound of structural formula (I) to be prepared, they are obtained, for example, by means of a process [variant (e)], characterized by the fact that a compound of structural formula (I) is reacted, in which symbol l represents a radical of structural formula -C (= A ¹ ) -B ¹ , where symbol A ¹ has a meaning as defined in structural formula (I) and symbol B ¹ has a meaning defined in a way analogous to the radical B ¹ in structural formula (I), with the exception of each of the symbols Q ¹ to Q ⁹ , in group B ¹ , representing a halogen atom, preferably a chlorine atom, with a thio compound of general formula HSR ³⁸ , and the desired compound of structural formula (I) may be optionally removed from the reaction mixture or isolated. Such methods are known, in principle, to those skilled in the art and are described, for example, in WO 2009/018925 (for example, page 21 in that document and details for process j) and in the literature cited therein.

[168] (f) The compounds of structural formula (I), and their salts, in which L represents a radical of structural formula -C (= A ¹ ) -B ¹ and B ¹ represents a group of formula structural (B10) [= compound (I-B10)] are also obtained, for example, by means of a process [variant (f)], characterized by the fact that a compound of structural formula (I) is reacted, in which the symbol L represents a radical of structural formula -C (= A ¹ ) -B *, the symbol A ¹ has a meaning as defined in structural formula (I) and the symbol B * represents a radical of structural formula -CH2- CO-R ²⁷ , where the R ²⁷ symbol

89/289 has the meaning defined in the structural formula (B10) [= compound (l-B)], Scheme

with et, Ν-dimethylformamide dimethylacetal to obtain the compound of structural formula (lC) (see diagram) and to react the compound (lC) with hydroxylamine ring closure, or its salts, to obtain the compound of structural formula (I-B10), where R ²⁸ = H or the compound (lB) is reacted with a compound of general formula (X1) HO-N = C (CI) -R ²⁸ (X1) where the symbol R ²⁸ has the meaning defined in structural formula (B10), with ring closure to obtain the compound of structural formula (I-B10), where symbol R ²⁸ in general formula (X1) has a meaning as defined in the compound of structural formula (I-B10) to be prepared, with the exception of R ²⁸ = H.

the reaction with dimethylacetal of Ν, Ν-dimethylformamide is known from analogous examples in EP 636622. Closing the ring with

90/289 hydroxylamine, or its salts, can be carried out, for example, in a suitable polar organic solvent, such as ethanol or acetonitrile, and, if appropriate, with base catalysis, preferably an organic base, such as triethylamine, at a temperature between 0 ° C and 150 ° C, and preferably between room temperature and the boiling point of the solvent in question; according to EP 636622.

(g) The compounds of structural formula (I), and their salts, in which L represents a radical of structural formula -C (= A ¹ ) -B ¹ and B ¹ represents a group of general formula (B10 ) [= compound (I-B10)] are also obtained, for example, according to a process [variant (g)], characterized by the fact that a compound of structural formula (II) is reacted

wherein the symbols A ¹ , (R ¹ ) m and (R ² ) n have the meanings as defined in structural formula (I) and Y represents a leaving group, preferably a halogen atom, and in particular an atom of chlorine, with a compound of formula X- (B10), where (B10) is defined as in group B ¹ and X represents a leaving group, preferably a halogen and, in particular, iodine, optionally in the presence of a coupling agent, to obtain the compound of structural formula (I) (inter-coupling reaction) or with an activated compound of structural formula X '- (B10), in which the symbol X' represents a metal or a group derived from a metal, preferably a Cl-Zn group, and (B10) is as defined in group B ¹ , to obtain the compound of formula (I).

[169] In this case, the activated compound X '- (B10) can be prepared, for

91/289 example, initially from the compound of formula X- (B10) referred to by reaction with metal or metal salts, for example, with Mg and Zn salts (compare with the following scheme).

Scheme

[170] The inter-coupling process between compound (II) and iodine- (B10), or similar intermediates, is optionally carried out using a coupling reagent. Suitable for this purpose are chemicals which are known to be suitable for coupling, for example, palladium reagents known from analogous reactions, such as tetrakis- (triphenylphosphine) palladium (O) in an analogous manner Negishi etal., Tetrahedron Lett. 24.1983,

5181).

[171] The process for the preparation of CIZn- (B10), or analogous compounds, can be carried out using suitable metals or metal derivatives. For example, for CIZn- (B10) the reaction of iodine- (B10) with magnesium chips and zinc chloride is suitable (see analogously to Knochel et al. Chem. A Eur. J. 15, 2009, 7192).

92/289 [172] The coupling process for the preparation of the compounds of structural formula (I-B10) is preferably carried out using one or more diluents. Suitable diluents include, in particular, organic solvents which are inert under the reaction conditions. These comprise, in particular, optionally halogenated aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride ; ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether; amides, such as N, N-dimethylformamide, N-methylpyrrolidone or hexamethylphosphoric triamide.

[173] When the coupling process is carried out, the reaction temperature can vary over a relatively wide range. In general, the process is carried out at a temperature between 0 ° C and 150 ° C and preferably between 10 ° C and 120 ° C. In general, the coupling is carried out at atmospheric pressure. However, it is also possible to carry out the process under high or reduced pressure - normally between 0.1 bar and 10 bar.

[174] (h) The compounds of formula (I), and their salts, in which the symbol L represents a radical of the structural formula -C (= A ² ) -B ² and the symbol B ² represents a radical of the formula structural OR ³³ or SR ³⁴ , are obtained, for example, through a process [variant (h)], characterized by the fact that a compound of structural formula (I ') is reacted

where the symbols (R ¹ ) m and (R ² ) n have the meanings defined in structural formula 25 (I), the symbol A ¹ represents an O or S radical and the symbol B ¹ represents a radical of structural formula (B1) , (B2), (B3), (B4), (B5), (B6), (B7),

93/289 (B8), (B9), (B11), (B12), (B13) or (B14) as defined above for compounds (I), where the symbol L represents a radical -C (= A ¹ ) -B ¹ , where each of the symbols Q ¹ to Q ⁹ , in the radicals B ¹ , represents OH or OM, with a compound of the general formula Y'-B ² , in which the symbol B ² has the defined meaning in the radical L and the symbol Y 'represents a leaving group, for example, chlorine, to obtain the compound (I), where the symbol B ² represents the radical OR ³³ (if A ¹ = O) or SR ³⁴ (if A ¹ = S), where the group C (= A ² ) - in the compound (I), compared to the group -CB ¹ in the compound (I '), represents the most stable tautomer or, preferably, a fixed tautomer under the structural point of view in which the radical -C (= A ² ) - corresponds tautomerically to the radical = C (-B ¹ ) -.

[175] Here, the expression “structurally fixed tautomer” means that in the radical -C (= A ² ) -B ² the group B ² represents a radical of the general formula OR ³³ or SR ³⁴ (that is, does not represent OH, OM, SH or SM).

[176] Depending on the meaning of the radical R ³³ or R ³⁴ , the compound of the general formula Y'-B ² is an alkylating agent, an acylating agent or an arylating agent. Therefore, the reaction can be carried out under conditions for alkylations, acylations or similar arylations, if appropriate in the presence of suitable catalysts (acids or bases) or, in particular, aryl catalysts.

[177] The compounds of structural formula (I), and their salts, in which the symbol L represents a radical of structural formula -C (= A ² ) -B ² and the symbol B ² represents a radical of structural formula -NR ^B R ^C , are obtained, for example, by means of a process [variant (i)], characterized by the fact that a compound of structural formula (I ') is reacted

A ¹ (R ¹ ) m

CN (R ² ) n (I ')

94/289 where the symbols (R ¹ ) m and (R ² ) do not have the meanings defined in the structural formula (I), the symbol A ¹ represents a radical of structural formula -NR ^B and the symbol B ¹ represents a radical of structural formula (B1), (B2), (B3), (B4), (B5), (B6), (B7), (B8), (B9), (B11), (B12), (B13) or (B14) as defined above for compounds (I), where the symbol L represents a radical -C (= A ¹ ) -B ¹ , where each of the symbols Q ¹ to Q ⁹ , in the radicals B ¹ , represents OH or OM, with a compound of the general formula Y'-R ^C , where the symbol R ^C has the meaning defined in the radical -NR ^B R ^C of the symbol B ² and the symbol Y 'represents a leaving group, for example , chlorine, to obtain compound (I), in which the symbol B ² represents the radical -NR ^B R ^C , in which the group -C (= A ² ) - in compound (I), compared to the group - CB ¹ in the compound (I '), represents the most stable tautomer or, preferably, a structurally fixed tautomer in which the radical -C (= A ² ) - c responds tautomerically to the radical = C (-B ¹ ) -.

[178] Here, the expression “structurally fixed tautomer” means that in the radical -C (= A ² ) -B ² the group B ² represents a radical of the general formula -NR ^B R ^C (that is, does not represent OH, OM, SH or SM).

[179] Other compounds of structural formula (I) according to the invention can be obtained in a process analogous manner known from compounds (I) according to the invention, by means of transformation. For example, hydroxylimino compounds of structural formula (I), in which the symbol A ¹ represents a radical of the general formula = N-OH, can optionally be obtained by the reaction of compounds (I), in which the symbol A ¹ represents an oxygen atom, with hydroxylamine.

[180] The compounds of structural formula (II) which have the reactive group -C (= A ¹ ) -Y, which are used to prepare the compounds (I) according to the invention by the variant (a), can be prepared from the corresponding carboxylic acids or carboxylic esters, that is, cyanobutyrates (III)

95/289

where the symbols (R ¹ ) m and (R ² ) n have the meanings defined by the structural formula (I) and the symbol R represents hydrogen or a hydrolyzable radical by transformation, for example, by preparation of halides, if the symbol

Y represents a halogen atom, in a manner analogous to known methods.

[181] The preparation of acid halides having the reactive group C (= O) -Hal, where the symbol Hal represents a halogen atom, preferably a chlorine atom, from carboxylic acids or carboxylic esters is known in principle by experts in the field; see, acid chloride from carboxylic acids using thionyl chloride, HoubenWeyl, Vol. VIII (1952), pages 359-680 or using oxalyl chloride according to Heterocycles, 26 (5), 1291-302; 1987.

[182] Similar processes are known for the preparation of other reactive groups -C (= A ¹ ) -Y.

[183] If the reactive group -C (= A ¹ ) -Y represents a group of general formula C (= NR ^A ) -Hal, then it may also be possible to use the corresponding carboxylic acids or carboxylic esters of structural formula (III ), where the symbol A ¹ represents an oxygen atom. In this case, the compounds that have the reactive group C (= O) -OR are initially subjected to reduction to obtain the compound that has the functional group alcohol (-CH2-OH) and then subjected to oxidation to obtain the compound that it has the aldehyde functional group (-C (= O) H) or they are subjected to reduction directly to obtain the compound that has the aldehyde functional group (-C (= O) H); for example, in a similar way to István E. Markó et al. Eur. J. Org. Chem. 2009, 1806.

[184] To prepare compounds that have the reactive group -C (= NR ^A ) 96/289

Hal, compounds having the aldehyde functional group (-C (= O) H) can then be halogenated, for example, in a manner analogous to R. A. Whitney et al. J. Org. Chem. 1988, 53, 4074; S. Kim et al. Chem. Commun. 2007, 4507; Chemistry-An Asian Journal 2008, 3, 1692; Chem. Commun. 2010, 46, 7822.

[185] The mixtures of diastereomers of the cyanobutyrates of structural formula (III) referred to are known in principle; see, for example, EPA 5341, EP-A 266725, EP-A270 830, JP 04/297454, JP 04/297455, JP 05/058979, WO 2011/003775, WO 2011/003776.

[186] In a manner analogous to the synthesis pathways described in the cited publications, the compounds can be prepared by standard organic chemistry processes.

[187] For example, compounds of formula (III) are obtained, characterized by the fact that (aa) compounds of formula (IV) are reacted (cyanomethyl benzene / phenylacetonitrile) (R ¹ ) m

ch ₂ -cn (IV) with compounds of formula (V) (derived from cinnamic acid) or their salts

(V) to obtain compounds of structural formula (III) (diastereomers / / racemic) in which the symbols A ¹ , R, R ¹ , R ² , men in compounds (IV) and (V) have the meanings defined in the compound structural formula (III) to be prepared.

97/289 [188] The starting materials (IV) and (V) necessary for the preparation of compounds (III) are known from the cited literature or can be prepared in a manner analogous to the cited literature.

[189] The reaction according to variant (aa) can be carried out, for example, according to methods and under conditions such as those known for Michael's additions. For example, the reaction is carried out at a temperature between -100 ° C and 150 ° C and, preferably, between -78 ° C and 100 ° C, in an organic or organic solvent, usually in the presence of a base or a catalyst or both [according to J. Chem. Soc. (1945), p. 438].

[190] Suitable solvents include, for example, organic solvents, such as:

- aliphatic hydrocarbons, such as pentane, hexane, cyclohexane or petroleum ether;

- aromatic hydrocarbons, such as toluene, o-, m- or p-xylene,

- halogenated hydrocarbons, such as methylene chloride, chloroform or chlorobenzene,

- ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran (THF),

- nitriles, such as acetonitrile or propionitrile,

- ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone,

- alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol and also

- dimethyl sulfoxide, dimethylformamide, dimethylacetamide, sulfolane,

- mixtures of the mentioned organic solvents.

[191] In individual cases, it is also appropriate to use inorganic solvents, such as water or mixtures of organic solvents with water.

[192] Preferred solvents include THF and methanol and mixtures with other organic solvents.

[193] The reaction via the preparation variant (aa) is preferably

98/289 carried out in the presence of a base, for example, from the set of inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, for example, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, oxides of alkali metals and alkaline earth metals, for example, lithium oxide, sodium oxide, calcium oxide or magnesium oxide, alkali metal and alkaline earth metal hydrides, for example, lithium hydride, sodium hydride , potassium hydride or calcium hydride, alkali metal amides, for example, lithium amide, sodium amide or potassium amide, alkali metal and alkaline earth metal carbonates, for example, lithium carbonate, potassium carbonate or calcium carbonate, alkali metal bicarbonates, for example, sodium bicarbonate, or organometallic compounds, such as, preferably, alkali metal alkyls, for example, methyl lithium, butyl lithium or phenyl lithium , alkylmagnesium halides, for example, methyl magnesium chloride, or alkali metal and alkaline earth metal alkoxides, for example, sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide or dimethoxy magnesium .

[194] The bases used can also be organic bases, for example, from the group consisting of tertiary aliphatic amines, for example, trimethylamine, triethylamine, tributylamine, diisopropylethylamine or N-methylpiperidine, or aromatic tertiary amines, for example, pyridine or substituted pyridines , such as collidine, lutidine or 4-dimethylaminopyridine, or bicyclic amines, such as 7-methyl-1,5,7-triazabicyclo [4.4.0] -dec-5-ene or 1,8diazabicyclo [5.4.0] undec- 7-ene (DBU).

[195] Preferred bases include, for example, potassium tert-butoxide, lithium bis- (trimethylsilyl) -amide or 7-methyl-1,5,7-triazabicyclo [4.4.0] -dec-5- eno.

[196] Generally speaking, the amount of base may vary within wide limits. For example, it may be expedient to use the base in catalytic amounts, in substoichiometric amounts, in equimolar amounts or in excess. A preferred liquid organic base can also optionally be used as a solvent.

99/289 [197] As suitable catalysts for the addition of Michael according to variant (aa) are acidic catalysts, for example, the set consisting of inorganic acids, for example, Broensted acids, such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acid or perchloric acid, or Lewis acids, such as boron trifluoride, aluminum trichloride, iron (III) chloride, tin (IV) chloride, titanium (IV) chloride, triflate scandium (III) or zinc (II) chloride, and also organic acids, for example, formic acid, acetic acid, propionic acid, oxalic acid, toluenesulfonic acid, benzene sulfonic acid, camphorsulfonic acid, citric acid or trifluoroacetic acid.

[198] In general, the amount of acidic catalyst can vary over wide limits. For example, it may be expedient to use the acid in catalytic amounts, in substoichiometric amounts, in equimolar amounts or in excess. A preferred liquid acid can also optionally be used as a solvent.

[199] For example, compounds of formula (III) are also obtained by a transesterification reaction, characterized by the fact that [200] (bb) compounds of formula (III ') are reacted

(III ') in which the symbol R' represents a radical of the group consisting of the possible radicals for the symbol R, but different from the radical R in the compound (III) to be prepared, with a compound of the general formula R-OH, in that the symbol R has the meaning defined in the structural formula (III), to obtain the compound (III), in which the symbols A ¹ , R ¹ , R ² , men in the compound (III ') have the meanings defined in the compound structural formula (III) to be prepared in each case.

[201] Transesterification reactions (bb) can be carried out, for example,

100/289 using a suitable R-OH alcohol in the presence of a catalyst, optionally in the presence of an aprotic solvent. In addition, in general, conditions are advantageous such that the chemical balance is shifted to the desired product side, for example, using a large excess of R-OH alcohol under virtually anhydrous conditions, for example, in the presence of a molecular sieve.

[202] In general, the reactions (transesterifications) can be carried out at a temperature between 0 ° C and 180 ° C and, preferably, between 20 ° C and 100 ° C, in the presence of a Lewis acid or of Broenstedt or an enzyme [according to J. Org. Chem. 2002, 67, 431].

[203] Suitable solvents include, for example, the following aprotic organic solvents:

- aliphatic hydrocarbons, such as pentane, hexane, cyclohexane or petroleum ether;

- aromatic hydrocarbons, such as toluene, o-, m- or p-xylene,

- halogenated hydrocarbons, such as methylene chloride (dichloromethane), chloroform or chlorobenzene,

- ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole or tetrahydrofuran (THF),

- nitriles, such as acetonitrile or propionitrile,

- ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone,

- dimethyl sulfoxide, dimethylformamide, dimethylacetamide or sulfolane, or

- mixtures of the organic solvents mentioned.

[204] The preferred solvent is R-OH alcohol, which is used simultaneously as a reaction partner for transesterification, optionally in combination with one of the mentioned aprotic organic solvents.

[205] Alternatively, it is also possible to obtain the desired ester from another ester in two steps by acidic or basic hydrolysis of the other esters in the free acid, that is, in compounds (III '), where the symbol R represents , on each

101/289 case, H, and subsequent esterification with an alcohol R-OH.

[206] The esterification from the free acid of structural formula (III ') / R = H can be carried out, for example, in a manner analogous to conventional methods, for example, at a temperature between 0 ° C and 120 ° C and preferably between 20 ° C and 50 ° C, optionally in the presence of a catalyst, in a substantially anhydrous medium or under conditions where the water, including water formed during esterification, is bound or otherwise any, removed. Suitable catalysts include anhydrous acids and bases and, preferably, organic acids or bases; see chemical process manuals for the esterification of carboxylic acids; see also, for example, J. Am. Chem. Soc. 2007, 129 (43), 13321; J. Org. Chem. 1984, 49 (22), 4287.

[207] Suitable solvents for esterification include the aprotic organic solvents mentioned above for process variant (bb), including R-OH alcohol, which is used simultaneously as a reaction partner for esterification, optionally in combination with one of the other mentioned aprotic organic solvents.

[208] Suitable catalysts for esterification include the acidic or basic bases or catalysts mentioned for the process variant (aa) (Michael addition), in an anhydrous form or with as low a water content as possible. Preferred catalysts include bases, lithium hydroxide, potassium carbonate, or organic amines such as pyridines, substituted pyridines and DBU.

[209] Any hydrolysis carried out before the esterification of other esters of structural formula (III '), in which the symbol R' represents, in each case, a different group of H, may be carried out in a manner analogous to conventional methods, for example, at a temperature comprised between 0 ° C and 120 ° C and preferably between 20 ° C and 50 ° C, if appropriate in the presence of a catalyst, in a medium / solvent containing water; see chemical process manuals for the hydrolysis of carboxylic esters; see also, for example, J. Am. Chem. Soc. 2007, 129 (43), 13321; J. Org. Chem. 1984, 49 (22), 4287.

102/289 [210] A suitable solvent for hydrolysis is water or an organic solvent containing water, for example, the mentioned organic solvents based on the mentioned process variant (aa) (Michael addition), preferably water or solvents polar organics that contain water, such as THF.

[211] Suitable catalysts for hydrolysis include the acids, bases or acidic or basic catalysts mentioned for the said process variant (aa) (Michael addition), containing, in each case, water. Preferred catalysts include aqueous acids and bases and, in particular, bases, such as lithium hydroxide, sodium hydroxide, potassium carbonate, pyridines, substituted pyridines and DBU, in the presence of organic solvents.

[212] Catalysts for esterification or hydrolysis can normally be used in catalytic quantities. In general, it is also possible to use relatively large amounts, including equimolar amounts and a molar excess. Often, use as a solvent is also possible.

[213] The reaction mixtures are processed in a conventional manner, for example, by mixing with water, phase separation and, if appropriate, chromatographic purification of impure products. Some of the intermediates and final products are obtained in the form of colorless or slightly brownish viscous oils which are purified or released from volatile components under reduced pressure and at a moderately high temperature.

[214] If intermediates and final products are obtained as solids, then purification can also be carried out by recrystallization or digestion. If the individual compounds (III ') or (III) cannot be obtained by the routes described above, then they can be prepared by transforming other compounds (III') or (III).

[215] To prepare stereochemically enriched compounds of structural formula (I), compounds (I) initially obtained as mixtures of diastereomers can be separated into stereoisomers.

[216] Alternatively, it may be possible to separate and enrich the

103/289 desired stereoisomers in the compounds (III) step, followed by enantioselective reactions up to the optically active compounds (I) step.

[217] The compounds of formulas (I) and (III) or (III ') contain two chirality centers at positions 2 and 3 of the valeronitrile backbone or positions 3 and 4 of the cyanobutyrate backbone and can contain one or more others chirality centers, depending on the substitution pattern.

[218] Due to the two mentioned chirality centers, there are 4 stereoisomers, namely two erythro enantiomers and two treo enantiomers.

[219] To prepare the compounds (I) according to the invention in the form of the preferred stereochemically enriched treo compounds or treo-2 compounds, it is necessary to enrich the treo compounds or the treo-2 stereoisomer (enantiomer) from the mixture of stereoisomers in a suitable manner. Therefore, an expedient process comprises the initial isolation of the isomers treo, treo-1 and treo-2, from the mixture of diastereomers (I), which further comprises the erythro isomers, and subsequent optical resolution with isolation or enrichment of the enantiomer treo-2 from the mixture with the treo-1 enantiomer.

[220] The isolation of threo isomers in the form of a racemic mixture can be carried out in a manner analogous to the conventional separation and purification processes mentioned above (separation of diastereomers).

[221] As suitable methods for the subsequent preparation of compounds of structural formula (I) in the form of stereochemically enriched treo-2 isomers are methods for optical resolution commonly known to those skilled in the art from analogous cases (according to manuals of stereochemistry), for example, using processes for separating mixture into diastereomers, for example, by means of physical processes such as crystallization, chromatographic processes, in particular, column chromatography and high performance liquid chromatography, distillation, if appropriate under reduced pressure, extraction and other processes, it is possible to separate mixtures

104/289 of remaining enantiomers, usually by chromatographic separation into solid chiral phases. Suitable for preparative quantities or for an industrial scale are processes such as crystallization of diastereomeric salts that can be obtained from mixtures of diastereomers using optically active acids and, if appropriate, provided that acidic groups are present, using optically bases active.

[222] Optically active acids suitable for optical resolution by crystallization of diastereomeric salts include, for example, camphorsulfonic acid, camphoric acid, bromochanphosulfonic acid, quinic acid, tartaric acid, dibenzoyltartaric acid and other similar acids; Optically active bases include, for example, quinine, cinconine, quinidine, brucine, 1- (S) - or 1- (R) -phenylethylamine and other similar bases.

[223] Crystallizations are then, in most cases, carried out in aqueous, alcoholic or aqueous-organic solvents, where the diastereomer which is less soluble precipitates first, if appropriate after addition of primary crystals. One enantiomer of the compound of formula (I) is then released from the precipitated salt, or the other is released from the crystals, either by acidification or by using a base.

[224] Therefore, the invention also provides the process for the preparation of treo-2 isomers of compounds (I), which is characterized by the fact that the compounds (I) are subjected to an optical resolution and the compound is isolated ( I) with a stereochemical purity between 60% and 100%, preferably between 70% and 100%, more preferably between 80% and 100% and, in particular, between 90% and 100%, based on the mixture of the threo enantiomers -2 gifts.

[225] As an alternative to the aforementioned optical resolution methods, enantioselective processes starting from stereochemically pure starting materials are also suitable, in principle, for the preparation of the treo2 (I) enantiomers.

[226] The following acids are usually suitable for the preparation of

105/289 acid addition salts of the compounds of structural formula (I): hydrohalogenic acids, such as hydrochloric acid or hydrobromic acid, as well as phosphoric acid, nitric acid, sulfuric acid, carboxylic acids and mono- or bi-functional hydroxycarboxylic acids , such as acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid or lactic acid, and also sulfonic acids, such as p-toluenesulfonic acid and 1,5-naphthalene disulfonic acid . The acid addition compounds of formula (I) can be obtained in a simple way by conventional methods for the formation of salts, for example, by dissolving a compound of formula (I) in a suitable organic solvent, such as , for example, methanol, acetone, methylene chloride or benzene, and addition of the acid at a temperature between 0 ° C and 100 ° C, after which they are isolated in a known manner, for example, by filtration and, if appropriate, subjected purification by washing with an inert organic solvent.

[227] The base addition salts of the compounds of formula (I) are preferably prepared in inert polar solvents, such as, for example, water, methanol or acetone, at a temperature between 0 ° C and 100 ° C. Examples of suitable bases for preparing the salts according to the invention include alkali metal carbonates, such as potassium carbonate, alkali metal and alkaline earth metal hydroxides, for example, NaOH or KOH, alkali metal hydrides and alkaline earth metal hydrides, for example, NaH, alkali metal alkoxides and alkaline earth metal alkoxides, for example, sodium methoxide or potassium tert-butoxide, or ammonia, ethanolamine or quaternary ammonium hydroxide of general formula [NRR ' R “R“ '] + OH'.

[228] What is meant by the term "inert solvents", referred to in the previous process variants, is, in each case, solvents that are inert under particular reaction conditions, but that do not need to be inert under all conditions reaction.

[229] The sets of compounds of structural formula (I) that can be

106/289 synthesized by the aforementioned process can also be prepared in a parallel way, being possible that this can take place manually, partially automated or fully automated. In this sense, it is possible to automate the reaction procedure, the processing or the purification of products and / or intermediates. In a global sense, this intends to designate a process as described, for example, by S. H. DeWitt in “Annual Reports in Combinatorial Chemistry and Molecular Diversity: Automated Synthesis”, Volume 1, Verlag Escom, 1997, pages 69 to 77.

[230] For the parallel reaction and processing procedure it is possible to use a range of commercially available instruments of the type provided, for example, by the companies Stem Corporation, Woodrolfe Road, Tollesbury, Essex, CM9 8SE, England, or H + P Labortechnik GmbH, Bruckmannring 28, 85764 OberschleiBheim, Germany. For the parallel purification of compounds (I) or intermediates produced during preparation, chromatography devices are available, inter alia, from ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA. The listed devices allow a modular procedure in which the individual process steps are automated, but between the process steps manual operations are required. This can be bypassed by using automated systems partially or fully integrated, in which the respective automation modules are operated, for example, by robots. Automation systems of this type can be purchased, for example, from Zymark Corporation, Zymark Center, Hopkinton, MA 01748, USA.

[231] In addition to the methods described here, the preparation of the compounds of formula (I) can be carried out, in whole or in part, by methods supported in solid phase. For this purpose, individual intermediates or all intermediates, in the synthesis or in a synthesis adapted for the corresponding process, are bonded to a synthetic resin. The methods of synthesis supported in solid phase are described extensively in the specialized literature, for example, Barry A. Bunin in “The

107/289

Combinatorial Index ”, Academic Press, 1998.

[232] The use of synthesis methods supported in solid phase allows different protocols to be carried out, which are known from the literature and which, in turn, can be executed manually or in an automated way. For example, the “tea bag method” (Houghten, US 4 631 211; Houghten et al., Proc. Natl. Acad. Sci, 1985, 82, 5131-5135), in which products from IRORI, 11149 North Torrey Pines Road, La Jolla, CA 92037, USA, are used, can be semi-automated. Automation of parallel synthesis supported in solid phase is carried out successfully, for example, by devices from Argonaut Technologies, Inc., 887 Industrial Road, San Carlos, CA 94070, USA or from MultiSynTech GmbH, Wullener Feld 4, 58454 Witten , Germany.

[233] The preparation according to the processes described here produces compounds of structural formula (I) in the form of collections or banks of substances. Accordingly, the present invention also provides banks of compounds of formula (I), which comprise at least two compounds of formula (I) and their precursors.

[234] The compounds of structural formula (I) according to the invention (and / or their salts), also referred to, before and after, together as "compounds according to the invention", "compounds (I) according to the invention ”or, for short, as“ compounds (I) ”, have an excellent herbicidal activity against a broad spectrum of harmful monocotyledonous and economically important dicotyledonous plants. The active compounds also have good control over harmful perennial plants that are difficult to control and produce shoots from rhizomes, rootstocks and other perennial organs.

[235] Therefore, the present invention also concerns a method for controlling unwanted plants or for regulating plant growth, preferably in plant cultures, in which one or more compounds according to the invention are applied to plants ( for example, harmful plants such as

108/289 as monocotyledonous or dicotyledonous weeds or unwanted crop plants), to seeds (for example, grains, seeds or vegetative propagules, such as tubers or bud parts with buds), to the soil in which the plants will grow (for example, the soil for cultivation or not for cultivation) or the area in which the plants grow (for example, the area under cultivation). The compounds according to the invention can be applied, for example, before cultivation (if appropriate also by incorporation into the soil), before emergence or after emergence. As specific examples, it is possible to mention some representative examples of monocotyledonous and dicotyledonous weed flower that can be controlled with the compounds according to the invention, without this enumeration being restricted to certain species.

[236] Harmful monocotyledonous plants of the genus: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharisis, Eleusine, Erusine, Eragine, Erusine, Erusine, , Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

[237] Dicotyledonous weeds of the genus: Abutilan, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emexim, Erysimum , Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rorippa, Rorippa, Rorippa, Rumippa , Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

[238] When the compounds according to the invention are applied to the soil surface before germination, then weed prevention and emergence of weed seedlings or weeds grow until they reach the cotyledonous stage, then stopping growth and,

109/289 eventually, after three to four weeks, they die completely.

[239] If the active compounds are applied after emergence to the green parts of the plants, then the growth is interrupted after the treatment and the harmful plants remain in the growing state of the moment of application or they die completely after a certain period of time, of a such that competition from weeds, which is harmful to crop plants, is thus eliminated in the beginning and in a prolonged way.

[240] Although the compounds according to the invention exhibit exceptional herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, for example, dicotyledonous crops of the genus Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus , Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous cultures of the genus Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicale, Saccharum, Seccharum Sorghum, Triticale, Triticum, Zea and, in particular, Zea and Triticum, are only damaged to an insignificant level or are not damaged at all, depending on the structure of the respective compound according to the invention and its rate of application. For these reasons, the present compounds are quite suitable for selective control of the growth of unwanted plants in crop plants, such as plants useful from an agricultural point of view or ornamental plants.

[241] In addition, the compounds according to the invention (depending on their particular structure and application rate used) have exceptional growth-regulating properties in crop plants. They intervene to regulate the plant's metabolism, so they can be used to influence plant constituents in a controlled way and to facilitate harvesting, for example, triggering desiccation and growth delay. In addition, they are also normally suitable for controlling and inhibiting growth

110/289 unwanted vegetation without destroying plants in the process. The inhibition of vegetative growth plays an important role in many monocot and dicot cultures, since it is possible, for example, to reduce lodging or prevent it completely.

[242] Due to their herbicidal properties and plant growth regulation, the active compounds can also be used to control harmful plants in crops of genetically modified plants or plants modified by conventional mutagenesis. In general, transgenic plants are distinguishable by their special advantageous properties, for example, by resistance to certain pesticides, in particular, of finished herbicides, resistance to plant diseases or to organisms that cause plant diseases, such as certain insects or microorganisms, such as fungi, bacteria or viruses. Other specific characteristics concern, for example, the material harvested with respect to quantity, quality, storage capacity, composition and specific constituents. Thus, transgenic plants are known whose starch content is increased or whose starch quality is altered or whose harvested material has a different fatty acid composition.

[243] With a view to transgenic crops it is preferable to use the compounds according to the invention and / or their salts in economically important transgenic crops of useful and ornamental plants, for example, cereals, such as wheat, barley, rye, oats , millet, rice and maize, or in crops of sugar beet, cotton, soy, rapeseed, potatoes, tomatoes, peas and other vegetables.

[244] It is preferable to use the compounds according to the invention as herbicides in useful plant cultures that are resistant or that have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.

[245] Due to their herbicidal and plant growth regulating properties, active compounds can also be used to control

111/289 harmful plants in crops of known genetically modified plants or of genetically modified plants yet to develop. In general, transgenic plants are distinguishable due to particularly advantageous properties, for example, by resistance to certain pesticides, mainly to certain herbicides, resistance to plant diseases or to organisms that cause plant diseases, such as certain insects or micro -organisms, such as fungi, bacteria or viruses. Other specific characteristics concern, for example, the material harvested with respect to quantity, quality, storage capacity, composition and specific constituents. Thus, transgenic plants are known whose starch content is increased or whose starch quality is altered or whose harvested material has a different fatty acid composition. Other particular properties may be tolerance or resistance to abiotic stress factors, for example, heat, low temperatures, drought, salinity and ultraviolet radiation.

[246] It is preferable to use the compounds of structural formula (I) according to the invention, or their salts, in economically important transgenic crops of useful plants and ornamental plants, for example, cereals, such as wheat, barley, rye, oats, sorghum and millet, rice, cassava and maize, or crops of sugar beet, cotton, soy, rapeseed, potatoes, tomatoes, peas and other vegetables.

[247] It is preferable to use the compounds of formula (I) according to the invention as herbicides in useful plant cultures that are resistant, or that have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.

[248] Conventional methods for generating new plants that have modified properties compared to plants that occur until today consist, for example, of conventional culture methods and the generation of mutants. Alternatively, it is possible to generate new plants with altered properties with the aid of recombinant methods (see, for example,

112/289 (eg EP-A-0221044, EP-A-0131624). For example, the following methods have been described in several cases:

- recombinant modifications of crop plants for the purpose of modifying the starch synthesized in plants (for example, documents WO 92/11376, WO 92/14827, WO 91/19806),

- transgenic crop plants that are resistant to particular herbicides of the glufosinate type (as per, for example, EP-A-0242236, EP-A242246) or the glyphosate type (WO 92/00377) or sulfonyl urea (EP documents -A-0257993, US-A-5013659),

- transgenic crop plants, for example, cotton, which is capable of producing Bacillus thuringiensis toxins (Bt toxins), which makes plants resistant to certain pests (documents EP-A-0142924, EP-A-0193259),

- transgenic crop plants with a modified fatty acid composition (WO 91/13972),

- genetically modified crop plants with new constituents or secondary metabolites, for example, new phytoalexins, which provide increased resistance to disease (documents EPA 309862, EPA0464461),

- genetically modified plants with reduced photorespiration that provide higher yields and greater tolerance to stress (document EPA 0305398),

- transgenic crop plants that produce important proteins from a pharmaceutical or diagnostic point of view (molecular pharmacology),

- transgenic crop plants that are distinguishable by higher yields and better quality,

- transgenic crop plants that are distinguishable by a combination, for example, of the aforementioned new properties (gene stacking).

[249] A large number of molecular biology techniques through which it is possible to generate new transgenic plants with modified properties are

113/289 known in principle; see, for example, I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg. or Christou, Trends in Plant Science 1 (1996) 423-431.

[250] For such recombinant manipulations, nucleic acid molecules that allow mutagenesis or a sequence change by recombination of DNA sequences can be introduced into plasmids. For example, it is possible to make basic substitutions, remove parts of strings or add natural or synthetic strings with the aid of conventional methods. For joining DNA fragments together, it is possible to attach adapters or ligands to the fragments; see, e.g., Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker Gene und Klone, VCH Weinheim, 2nd edition, 1996.

[251] The production of plant cells with reduced activity of a gene product can be achieved, for example, through the expression of at least one suitable antisense RNA or one sense RNA to obtain a co-effect. - suppression or else through the expression of at least one properly constructed ribozyme that cleaves specifically transcripts of the aforementioned gene product.

[252] To this end, it is possible, first, to use DNA molecules that comprise the complete coding sequence of a gene product, including any flanking sequences present, or else DNA molecules that comprise only parts of the coding sequence , in which case such parts should be long enough to provide an antisense effect on the cells. It is also possible to use DNA sequences that have a high degree of homology with the coding sequences of a gene product, but that are not completely identical.

[253] When nucleic acid molecules are expressed in plants, the synthesized protein can be located in any desired cell compartment

114/289 of the plant. However, to achieve localization in a particular compartment, it is possible, for example, to link the coding region with DNA sequences that guarantee the location in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). Nucleic acid molecules can also be expressed in the organelles of plant cells.

[254] Cells from transgenic plants can be regenerated using known techniques to obtain complete plants. In principle, transgenic plants can be plants of any desired plant species, that is, monocotyledonous and dicotyledonous plants.

[255] Thus, it is possible to obtain transgenic plants whose properties are altered by overexpression, suppression or inhibition of genes or sequences of homologous genes (= natural) or by expression of genes or heterologous gene sequences (= exogenous).

[256] It is preferable to use the compounds (I) according to the invention in transgenic cultures that are resistant to growth regulators, such as, for example, dicamba, or against herbicides that inhibit essential plant enzymes, for example, acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxigenases (HPPD), or against herbicides from the set of sulfonylureas, glyphosate, glufosinate or benzoylisoxazoles and similar active compounds.

[257] During the use of the active compounds according to the invention in transgenic cultures, there are not only the effects against harmful plants observed in other cultures, but often also effects that are specific to the application in the particular transgenic culture, for example, an altered or specifically broad spectrum of weeds that can be controlled, altered application rates that can be used for application, frankly good combinability with the herbicides for which the crop

Transgenic 115/289 is resistant and has an influence on the growth and yield of transgenic crop plants.

[258] Therefore, the invention also concerns the use of the compounds of structural formula (I) according to the invention and / or their salts as herbicides for the control of harmful plants in useful or ornamental plant cultures, optionally in transgenic crop plants.

[259] Pre-emergence or post-emergence use is preferred in cereals, such as wheat, barley, rye, oats, millet and rice and, in particular, in wheat by the post-emergence method.

[260] Pre-emergence or post-emergence methods for maize and, in particular, pre-emergence methods for maize are also preferred.

[261] It is also preferred to use the pre-emergence or post-emergence method on soybeans and, in particular, the post-emergence method in play.

[262] The use according to the invention to control harmful plants or to regulate plant growth also comprises the case where the active compound of structural formula (I), or a salt thereof, is not formed from a substance precursor (“prodrug”) until a moment after application on the plant, plant or soil.

[263] The invention also provides the method (method of application) to control harmful plants or to regulate the growth of plants which comprises the application of an effective amount of one or more compounds of structural formula (I), or their salts, in plants (harmful plants, if appropriate in conjunction with useful plants), in plant seeds, in the soil on which the plants will grow, or in the area under cultivation.

[264] The compounds (I) according to the invention can be used in the form of wettable powders, emulsifiable concentrates, spray solutions, products for the application of dust or granules in conventional formulations. Accordingly, the invention also provides herbicidal and plant growth regulating compositions comprising the compounds of structural formula (I) and / or their salts.

116/289 [265] Therefore, the compounds of structural formula (I), and / or their salts, can be formulated in several ways, according to which biological and / or physicochemical parameters are necessary. Possible formulations include, for example: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water emulsions and water-in-oil, sprayable solutions, suspension concentrates (SC), dispersions based on oil or water, oil-miscible solutions, capsule suspensions (CS), dust products (DP), products for seed coating, granules for spreading or application to the soil granules, granules (GR) in the form of microgranules, sprayable granules, coated granules and granules for adsorption, water dispersible granules (WG), water soluble granules (SG), formulations ULV, microcapsules and waxes.

[266] This individual formulation types are known in principle and are described, for example, in: Winnacker-Küchler, Chemische Technologie [Chemical Technology], Volume 7, C. Hanser Verlag Munich, 4th ed. 1986; Wade van Valkenburg, Pesticide Formulations, Marcel Dekker, NY, 1973; K. Martens, Spray Drying Handbook, 3rd ed. 1979, G. Goodwin Ltd. London.

[267] Necessary formulation aids, such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in: Watkins, Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Darland Books , Caldwell NJ, Hv Olphen, Introduction to Clay Colloid Chemistry; 2nd Ed., J. Wiley & Sons, N.Y .; C. Marsden, Solvents Guide; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's Detergents and Emulsifiers Annual, MC Publ. Corp., Ridgewood N.J .; Sisley and Wood, Encyclopedia of Surface Active Agents, Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt, Grenzflachenaktive Athylenoxidaddukte [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesell., Stuttgart 1976; WinnackerKüchler, Chemische Technologie, volume 7, C. Hanser Verlag Munich, 4th ed.

117/289

1986.

[268] Humectable powders are preparations that can be dispersed evenly in water and, as well as the active compound, in addition to a diluent or inert substance, also comprise ionic and / or non-ionic surfactants (wetting agents, dispersants), for example, polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, polyglycolic fatty ether sulphates, alkanesulphonates, alkylbenzenesulphonates, sodium lignosulphonate, 2,2'-dinaftymethane-6,6'-disulfonate sodium dibutylnaphthalene sulfonate or sodium oleoylmethyltaurinate. To prepare the humectable powders, the herbicide-active compounds are finely ground, for example, in conventional appliances, such as hammer mills, blow mills and air jet mills, and, simultaneously or subsequently, mixed with formulation aids.

[269] Emulsifiable concentrates are produced by dissolving the active compound in an organic solvent, for example, butanol, cyclohexanone, dimethylformamide, xylene or else high-melting aromatic or hydrocarbons or mixtures of organic solvents, with the addition of one or more ionic and / or non-ionic surfactants (emulsifiers). The emulsifiers used can be, for example: alkyl alkylarylsulfonic salts, such as calcium dodecylbenzene sulphonate, or nonionic emulsifiers, such as polyglycolic fatty esters, alkylaryl-polyglycolic ethers, polyglycolic ethers of fatty alcohols, condensation products of propylene oxide ethylene oxide, alkyl polyethers, sorbitan esters, such as, for example, sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, such as, for example, polyoxyethylene sorbitan fatty acid esters.

[270] Dust products are obtained after grinding the active compound with finely distributed solid substances, for example talc, natural clays, such as kaolin, bentonite or pyrophyllite, or diatomaceous earth.

118/289 [271] Suspension concentrates can be based on oil or water. These can be produced, for example, by wet grinding using commercial ball mills with optional addition of surfactants, such as those mentioned above, for example, for other types of formulation.

[272] Emulsions, eg oil-in-water (EW) emulsions, can be prepared, for example, by means of agitators, colloid mills and / or static mixers, using aqueous organic solvents and, if appropriate, surfactants, such as, for example, those already listed for other types of formulation.

[273] Granules can be produced by spraying the active compound onto an inert granular adsorptive material or by applying active compound concentrates by means of adhesives, for example, polyvinyl alcohol, sodium polyacrylate or mineral oils, on the surface of vehicles, such as sand, kaolinites or granulated inert materials. Suitable active compounds can also be granulated in a conventional manner for the production of fertilizer granules - if desired in the form of a mixture with fertilizers.

[274] Water-dispersible granules are usually produced by conventional processes, such as spray drying, fluidized bed granulation, plate granulation, mixing in high-speed mixers and extrusion in the absence of solid inert material.

[275] For the production of granules by plates, granules by fluidized bed, granules by extrusion and granules by spraying, see, for example, processes in Spray-Drying Handbook 3 ^a ed. 1979, G. Goodwin Ltd., London; JE Browning, Agglomeration, Chemical and Engineering 1967, pages 147 ff .; Perry's Chemical Engineer's Handbook, 5th Ed., McGraw-Hill, New York 1973, p. 8-57.

[276] For more details regarding the formulation of crop protection agents, see, for example, GC Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pages 81- 96 and JD

119/289

Freyer, SA Evans, Weed Control Handbook, 5th ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

[277] In general, agrochemical formulations comprise between 0.1% and 99% by weight and, in particular, between 0.1% and 95% by weight of active compound of structural formula (I) and / or their salts.

[278] In humectable powders, the concentration of active compound is, for example, between about 10% and 90% by weight; the remainder up to 100% by weight consists of conventional formulation constituents. In the case of emulsifiable concentrates, the concentration of active compound can be between about 1% and 90% and preferably between 5% and 80% by weight. Dust-type formulations contain between 1% and 30% by weight of active compound and, preferably, normally between 5% and 20% by weight of active compound; sprayable solutions contain between about 0.05% and 80% by weight and, preferably, between 2% and 50% by weight of active compound. In the case of water-dispersible granules, the active compound content depends, in part, on whether the active compound is present in a liquid or solid form and on the type of granulation aids, fillers, etc., are used. In water-dispersible granules, the active compound content is, for example, between 1% and 95% by weight and preferably between 10% and 80% by weight.

[279] In addition, the active compound formulations referred to include, optionally, the respective adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, vehicles and dyes, antifoam agents, inhibitors evaporation agents and agents that influence pH and viscosity. Examples of formulation aids are described, inter alia, in Chemistry and Technology of Agrochemical Formulations, ed. D. A. Knowles, Kluwer Academic Publishers (1998).

[280] The compounds of structural formula (I), or their salts, can be used as is or in the form of their preparations (formulations)

120/289 combined with other pesticide-active compounds, such as, for example, insecticides, acaricides, nematicides, herbicides, fungicides, phytoprotective agents and / or growth regulators, for example in the form of a finished formulation or tank mixes. Combination formulations can be prepared based on the above formulations, taking into account the physical properties and stability of the active compounds to be combined.

[281] As active compounds that can be used in combination with the compounds according to the invention in mixed formulations or in tank mixes, there are, for example, known active compounds that are based on the inhibition, for example, of acetolactate synthase , acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshiquimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxigenase, phytene desaturase, photositema I, photositema II, protoporphyrinogen oxidase, as described, for example, in 44 Weed Research 26 (1) -445 or the Pesticide Manual, 15th edition, the British Crop Protection Council and the Royal Soc. of Chemistry, 2006 and literature cited therein. Known herbicides or plant growth regulators that can be combined with the compounds according to the invention are, for example, the following active compounds (the compounds are designated by the common name according to the 'International Organization for Standardization' (ISO) or by chemical name or code number) and always include all forms of use, such as acids, salts, esters and isomers, such as stereoisomers and optical isomers. In this case, one or so, in some cases, more than a form of use is mentioned by way of example:

acetochlor, acibenzolar, acibenzolar-S-methyl, acifluorfen, acifluorfen-sodium, aclonifene, alachlor, alidochlor, aloxidim, aloxidim-sodium, ametrine, amicarbazone, amidochlor, starch-sulfurone, aminocyclopyracloride, aminocyclopyracloride, aminocyclopyracloride, aminocyclopyracloride amitrole, ammonium sulfamate, ancimidol, anilophos, asulam, atrazine, azafenidin,

121/289 azimsulfurone, aziprotrin, beflubutamide, benazoline, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulide, bensulfuroa, bensulfuronamethyl, bentazone, benzfendizone, benzobicyclone, benzofenap, benzofluorine, benzofluoride, benzofluorine, benzofluorine, benzofluorine, , bispyribac-sodium, bromacyl, bromobutide, bromophenoxy, bromoxynil, bromurone, bumina, busoxinone, butachlor, butafenacil, butamiphos, butenachlor, butralin, butroxidim, butylate, cafenstrole, chloretifen, chloromethamone, chlorofon -butyl, chlorbromurone, chlorinate, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazone, chlorimurone, chlorimurone-ethyl, chlormequat-chloride, chlornitrophen, chlorophthalim, clortalone-chlorethone, chlorhlorurone, chlorhlorurone , cinmethyline, cinosulfurone, cletodim, clodinafop, clodinafop-propargyl, clofencet, clofencet-potassium, clomazone, clomeprop, cloprop, clopyralides, chloransulam, chloransulam-methyl, cumilurone, cyanamide, cyanazine, cyclanilide, cyclate, cyclo-sulfamurone, cycloxidine, cyclurone, cy-halofop, cy-halofop-butyl, cyperquat, cyprazine, cyprazole,

2,4-D, 2,4-DB, daimurone / dimron, dalapone, daminozide, dazomet, n-decanol, demedipham, desmethrin, detosyl-pyrazolate (DTP), dialate, dicamba, diclobenyl, dichorprop, diclorprop-P, diclofopop , diclofop-methyl, diclofop-P-methyl, diclosulam, diethyl, diethyl-ethyl, diphenoxurone, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, diquegulac-sodium, dimefurone, dimepiperate, dimetamine, dimetamine, dimetamine, dimetamethine, dimethamethine, dimethamethine, dimethamethine, dimethamethine, dimethamethine , dimetrasulfurone, dinitramine, dinoseb, dinoterb, diphenamide, dipropetrin, diquat, diquatdibromide, dithiopir, diurone, DNOC, eglinazine-ethyl, endothal, EPTC, esprocarb, ethalfluraline, etametsulfurone, etametsulfurone, etametsulfone, methylamide , ethoxyfen-ethyl, ethoxysulfurone, etobenzanide, F5331, i.e., N- [2-chloro-4-fluoro-5- [4- (3-fluoropropyl) -4,5-dihydro-5-oxo-1Htetrazol- 1-yl] -phenyl] -ethanesulfonamide, F-7967, i.e., 3- [7-chloro-5-fluoro-2 (trifluoromethyl) -1H-benzimidazol-4-yl] -1-methyl-6- (trifluoro methyl) -pyrimidine2,4 (1H, 3H) -dione, fenoprop, phenoxaprop, phenoxaprop-P, phenoxaprop-ethyl,

122/289 fenoxaprop-P-ethyl, fenoxasulfone, fentrazamide, fenurone, flamprop, flampropM-isopropyl, flamprop-M-methyl, flazasulfurone, florasulam, fluazifop, fluazifopP, fluazifop-butyl, fluazifop-P-butyl, flazbone, flazbone, flazbone , flucetosulfurone, flucloraline, flufenacet (thiafluamide), flufenpir, flufenpirethyl, flumetraline, flumetsulam, flumiclorac, flumiclorac-pentila, flumioxazin, flumipropine, fluometurone, fluorodiphen, fluoroglycofur, fluoroglycofur, fluoroglycofur, fluoroglycofur sodium, flurenol, flurenol-butyl, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurprimidol, flurtamone, flutiacet, flutiacet-methyl, flutiamide, fomesafen, foramsulfurone, forclorfenurone, phosphol, gluten, gluten, furyloxifen -P, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-isopropylammonium, H-9201, that is, isopropylphosphoramidothioate d and O- (2,4-dimethyl-6-nitrophenylp) -O-ethyl, halosaphen, halosulfurone, halosulfurone-methyl, haloxifop, haloxifop-P, haloxifop-ethoxyethyl, haloxifop-P-ethoxyethyl, haloxifop-P, haloxifop-P, haloxifop-P -methyl, hexazinone, HW-02, i.e., 1- (dimethoxyphosphoryl) (2,4-dichlorophenoxy) -ethyl, imazametabenz, imazametabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapir, imazapyr-isopropylammon, imazaquine, imazaquine-ammonium, imazetapyr, imazetapyr-ammonium, imazosulfurone, inabenfide, indanophane, indaziflam, indoleacetic acid (IAA), 4-indol-3-ylbutyric acid (IBA), iodosulfurone, iodo sulfuronamide, sodium sulfuronamethyl ioxynyl, ipfencarbazone, isocarbamide, isopropaline, isoproturone, isourone, isoxabene, isoxaclortole, isoxaflutole, isoxapyrifop, KUH-043, that is, 3 - ({[5- (difluoromethyl) -1-methyl-3 (trifluoromethyl) -trifluoromethyl) -1 pyrazol-4-yl] -methyl} -sulfonyl) -5,5-dimethyl-4,5-dihydro-1,2oxazole, carbutylate, ketospiradox, lactophen, lenacil, linurone, hydrazide leica, MCPA, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecopropsodium, mecoprop-butotyl, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethyl-hexyl, mecoprop-P- potassium, mefenacet, mefluidide, mepiquat-chloride, mesosulfurone, mesosulfurone-methyl, mesotrione, metabenztiazurone, metam, metamifop, metamitron, metazachlor,

123/289 metazasulfurone, metazole, methypyrosulfurone, methiozoline, methoxyphenone, methyldimron, 1-methyl-cyclopropene, methyl isothiocyanate, metobenzurone, metobromurone, metolachlor, S-metolachlor, metosulam, methoxyurone, methulfone, methyzurine, metribuzine , monocarbamide, monocarbamide dihydrogen sulfate, monolinurone, monosulfurone, monosulfurone ester, monurone, MT-128, ie 6-chloro-N - [(2E) -3-chloroprop-2-ene-1yl] -5- methyl-N-phenylpyridazine-3-amine, MT-5950, that is, N- [3-chloro-4- (1-methylethyl) phenyl] -2-methyl-pentanamide, NGGC-011, naproanilide, napropamide, naptalam, NC-310, ie 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzylaxypyrazole, neburone, nicosulfurone, nipyraclofen, nitralin, nitrophen, nitrophenolate-sodium (mixture of isomers), nitrofluorfen, nonanoic acid, norflurazone , orbencarb, ortosulfamurone, orizalina, oxadiargilo, oxadiazone, oxasulfurone, oxaziclomefona, oxifluorfen, paclobutrazole, paraquat, paraquat dichloride, pelaric acid gonic (nonanoic acid), pendimethalin, pendralin, penoxsulam, pentanochlor, pentoxazone, perfluidone, petoxamide, fenisofam, fen-medifam, fen-medifam-ethyl, picloram, picolinafen, pinoxadene, piperofos, pirifenop, pirifenop, pyriphenyl, pyriphenyl, pyriphenyl, pyriphenyl, pyriphenyl, pyriphenyl primisulfurone-methyl, probenazole, profluazole, prociazine, prodiamine, prifluralin, profoxidim, prohexadione, prohexadione-calcium, prohexadione-calcium, prohydrojasmone, promethazine, propachlor, propanyl, propaquizafop, propazine, profam, propisochlor, propoxybazone, propoxycarbazone, propoxicarbazone propyrisulfurone, propizamide, prosulfalin, prosulfocarb, prosulfurone, prinachlor, pyraclonyl, piraflufene, piraflufene-ethyl, pirasulfotole, pyrazolinate (pyrazolate), pyrazosulfurone, pyrazosulfurone-ethyl, pyrazoxifene, pyribambyr, pyribambyr, pyribambyr, pyribambyr, pyribambyr, pyribambyr, pyribambyr, pyribambyr, pyribambyr, pyribambyr , pyridate, pyriftalide, pyriminobac, pyriminobacmethyl, pyrimisulfan, piritiobac, piritiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuril, rimsulfurone, saflufenacil, secbumetone, setoxidim, sidurone, simazine, it is, 2R) Methyl 2 - ({7- [2-chloro-4- (trifluoromethyl) -phenoxy] -2-naphthyl} -oxy) -propanoate,

124/289 sulcotrione, sulfalate (CDEC), sulfentrazone, sulfometurone, sulfometuronamethyl, sulfosate (glyphosate-trimesium), sulfosulfurone, SW-065, SYN-523, SYP249, that is, 5- [2-chloro-4- (trifluoromethyl) -phenoxy] -2-1-ethoxy-3-methyl1-oxobut-3-ene-2-yl, 2-nitrobenzoate, SYP-300, ie 1- [7-fluoro-3-oxo-4- (prop-2 -ino-1-yl) -3,4-dihydro-2H-1,4-benzoxazine-6-yl] -3-propyl-2-thioxo-imidazolidine-4,5-dione, tebutam, tebutiurone, tecnazene, tefuriltrione , tembotrione, tepraloxidim, terbacil, terbucarb, terbuclor, terbumetone, terbutilazine, terbutrin, tenilchlor, thiafluamide, thiazaflurone, thiazopyr, tidiazimine, tidiazurone, thienocarbazone, thienocarbazone, thienocarbazone-thienocarbazone-thienocarbazone-thienocarbazone-thienocarbazone , trialate, triasulfurone, triaziflam, triazophenamide, tribenurone, tribenurone-methyl, trichloroacetic acid (TCA), triclopyr, tridiphane, trietazine, trifloxysulfurone, trifloxysulfurone-sodium, trifluraline, triflusulfurone, triflusulfurone ulfurone-methyl, trimeturone, trinexapac, trinexapac-ethyl, tritosulfurone, tsitodef, uniconazole, uniconazole-P, vernolate, ZJ-0862, that is, 3,4-dichloro-N- {2 - [(4,6-dimethoxypyrimidine- 2-yl) -oxy] -benzyl} -aniline and the following compounds:

[282] The selective control of harmful plants in crops of useful and ornamental plants is particularly interesting. Although the compounds (I) according to the invention have already shown very good selectivity to be suitable in different cultures, in principle, in some cultures and, in particular, also in the case of mixing with other less selective herbicides, they can

125/289 phytotoxicities occur in crop plants. In this sense, combinations of compounds (I) according to the invention that comprise compounds (I), or their combinations, with other herbicides or pesticides and phytoprotective agents are particularly interesting. Phytoprotective agents, which are used in an antidote-effective amount, reduce the phytotoxic side effects of herbicides / pesticides used, for example, in economically important crops, such as cereals (wheat, barley, rye, corn) , rice, millet), sugar beet, sugar cane, rapeseed, cotton and soy and, preferably, cereals. The following groups of compounds are suitable, for example, as phytoprotective agents for compounds (I) and their combinations with other pesticides.

[283] A) Structural formula (SI) compounds (Ra ¹ U

W 'R _A (SI) where the symbols and indices have the following meanings:

the symbol nA represents a natural number between 0 and 5 and preferably between 0 and 3;

the symbol Ra ¹ represents halogen, alkyl (C1-C4), alkoxy (C1-C4), nitro or haloalkyl (C1-C4);

the symbol Wa represents a divalent unsubstituted or substituted heterocyclic radical from the set of heterocycles with five partially unsaturated or aromatic members that have between 1 and 3 heteroatoms in the N or O ring, in which at least one nitrogen atom and at most one oxygen atom are present in the ring and preferably a radical from the group (Wa ¹ ) to (Wa ⁴ ),

(Wa ² ) (Wa ³ )

126/289 the mA symbol represents 0 or 1;

the symbol Ra ² represents ORa ³ , SRa ³ or NRa ³ Ra ⁴ or a saturated or unsaturated 3 to 7 membered heterocycle that has at least one nitrogen atom and up to 3 hetero atoms, preferably from the set consisting of O and S, the which is attached to the carbonyl group in (SI) via the nitrogen atom and is unsubstituted or substituted with radicals from the group consisting of alkyl (C1 -C4), alkoxy (C1-C4) or optionally substituted phenyl, preferably a radical of formula general ORa ³ , NHRa ⁴ or N (CH3) 2 and, in particular, of the general formula ORa ³ ;

Ra ³ represents hydrogen or an unsubstituted or substituted aliphatic hydrocarbyl radical that preferably has a total of 1 to 8 carbon atoms;

the symbol Ra ⁴ represents hydrogen, alkyl (Ci-Ce), alkoxy (Ci-C6) or substituted or unsubstituted phenyl;

the symbol Ra ⁵ represents H, alkyl (Ci-Ce), haloalkyl (Ci-C8), alkoxy (Ci-C4) alkyl (Ci-Ce), cyano or COORa ⁹ , where the symbol Ra ⁹ represents hydrogen, alkyl ( C1-Ce), haloalkyl (C1-C), alkoxy (C1-C4) -alkyl (C1-C4), hydroxyalkyl (C1-C6), cycloalkyl (C3-C2) or tri-alkyl (C1-C4) -silyl;

the symbols Ra ⁶ , Ra ⁷ , Ra ⁸ are identical or different and represent hydrogen, alkyl (Ci-Ce), haloalkyl (Ci-Ce), cycloalkyl (C3-Ci2) or substituted or unsubstituted phenyl;

preferably:

a) ethyl dichlorophenylpyrazoline-3-carboxylic acid compounds, preferably compounds such as ethyl 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylate (mefenpir-diethyl, see Pestic. Man.), and associated compounds, as described in WO 91/07874;

b) dichlorophenylpyrazolecarboxylic acid derivatives, preferably compounds such as ethyl 1- (2,4-dichlorophenyl) -5-methylpyrazole-3-carboxylate (S1-2), 1- (2,4-dichlorophenyl) -5-isopropylpyrazole Ethyl (S1-3) -3-carboxylate, ethyl (S-4-2,4- dichlorophenyl) -5- (1,1-dimethylethyl) -pyrazole-3-carboxylate, 1- (2,4127 / 289 ethyl dichlorophenyl) -5-phenylpyrazole-3-carboxylate (S1-5) and associated compounds, as described in EP-A-333 131 and EP-A-269 806;

c) triazolecarboxylic acid type compounds, preferably compounds such as fenclorazole (-ethyl), i.e., 1- (2,4-dichlorophenyl) -5-trichloromethyl- (1H) -1,2,4 triazole-3-carboxylate ethyl (S1-6) and associated compounds, as described in EP-A-174 562 and EP-A-346 620;

d) compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid type or of the 5,5-diphenyl-2-isoxazoline-3-carboxylic acid type, preferably compounds such as 5- (2, Ethyl 4-dichlorobenzyl) -2-isoxazoline-3-carboxylate (S1-7) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-8) and associated compounds, as described in WO 91/08202, or Ethyl 5,5-diphenyl-2isoxazolinecarboxylate (isoxadifene-ethyl) or n-propyl 5,5-diphenyl-2isoxazolinecarboxylate (S1-10) or 5- (4-fluorophenyl) -5-phenyl-2isoxazoline -3-ethyl carboxylate (S1-11), as described in patent application No. WO-A-95/07897.

[284] B) Quinoline derivatives of structural formula (S-II)

where symbols and indices have the following meanings:

Rb ¹ represents halogen, alkyl (C1-C4), alkoxy (C1-C4), nitro or haloalkyl (C1-C4);

nB represents a natural number between 0 and 5 and, preferably, between 0 and 3;

the symbol Rb ² represents ORb ³ , SRb ³ or NRb ³ Rb ⁴ or a saturated or unsaturated 3- to 7-membered heterocycle that has at least one nitrogen atom and up to 3 hetero atoms, preferably selected from the group consisting of O and S , which is joined to the carbonyl group in (S-II) through the nitrogen atom and is unsubstituted or substituted with radicals of the group

128/289 consisting of (C 1 -C 4) alkyl, (C 1 -C 4) alkoxy or optionally substituted phenyl, preferably a radical of the general formula ORb ³ , NHRb ⁴ or N (CH 3) 2 and in particular the general formula ORb ³ ;

Rb ³ represents hydrogen or an unsubstituted or substituted aliphatic hydrocarbyl radical which preferably has a total of 1 to 18 carbon atoms;

Rb ⁴ represents hydrogen, substituted or unsubstituted (C 1 -C 6), alkoxy (C 1 -C 6) or phenyl;

Tb represents an alkanediyl chain (C1 or C2) which is unsubstituted or substituted with one or two alkyl (C1 -C4) radicals or with [alkoxy (C1-C3)] carbonyl; preferably:

a) 8-quinolinoxyacetic acid (S2) type compounds, preferably 1-methylhexyl (5chloro-8-quinolinoxy) -acetate (common name cloquintocet15 mexilo (S2-1) (see Pestic. Man.), ( 1,3-dimethylbut-1-yl (S2-2) 5-chloro-8-quinolinino) -acetate, (5-chloro-8-quinolinoxy) -4-allyloxybutyl acetate (S2-3), (5- 1-allyloxyprop-2-yl chloro-8-quinolinoxy) -acetate (S2-4), (5-chloro-8-quinolinoxy) ethyl acetate (S2-5), (5-chloro-8-quinolinoxy) -acetate 2- (220 propylidene-iminoxy) -1-ethyl (S2-6), allyl (5-chloro8-quinolinoxy) -acetate (S2-7), 2- (220 propylidene-iminoxy) -1-ethyl acetate (S2 -8), 2-oxo-propyl-yl (5-chloro-8-quinolinoxy) -acetate (S2-9) and associated compounds, as described in EP-A86 750, EP-A-94 349 and EP- A-191 736 or EP-A-0 492 366, and also their hydrates and salts, as described in document W0-A-2002/034048,

b) compounds of the type (5-chloro-8-quinolininoxy) -malonic acid, preferably compounds such as diethyl (5-chloro-8-quinolinino) -malonate, (5-chloro-8quinolininoxy) -dialmalonate, Methyl-ethyl (5-chloro-8-quinolinino) -malonate and associated compounds, as described in EP-A-0 582 198.

[285] C) Compounds of structural formula (S-III)

129/289

The ijk / ^R c ²

Rp N ^{c c} I ¹ 3

Rc in which the symbols and indices have the following meanings:

Rc ¹ represents alkyl (C1-C4), haloalkyl (C1-C4), alkenyl (C2-C4), haloalkenyl (C2-C4), cycloalkyl (C3-C7) and, preferably, dichloromethyl; the symbols Rc ² , Rc ³ are identical or different and represent hydrogen, alkyl (C-C4), alkenyl (C2-C4), alkynyl (C2-C4), haloalkyl (C-C4), haloalkenyl (C2-C4), alkyl (C1-C4) -carbamoyl-alkyl (C1-C4), alkenyl (C2-C4) carbamoyl-alkyl (C1-C4), alkoxy (C1-C4) -alkyl (C1-C4), dioxolanylalkyl (Ci -C4), thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or the symbols Rc ² and Rc ³ together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine, thiazolidine ring, piperidine, morpholine, hexahydropyrimidine or benzoxazine; preferably:

active compounds of the dichloroacetamide type that are often used as pre-emergence phytoprotective agents (phytoprotective agents active in the soil), such as, for example, dichloride (see Pestic. Man.) (= N, N-diallyl-2,2-dichloroacetamide ),

R-29148 (= Stauffer's 3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine),

R-28725 (= Stauffer's 3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine),

Benoxacor (see Pestic. Man.) (= 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4benzoxazine),

PPG-1292 (= N-allyl-N - [(1,3-dioxolane-2-yl) -methyl] -dichloroacetamide from PPG Industries),

DKA-24 (= N-allyl-N - [(allylaminocarbonyl) -methyl] -dichloroacetamide from SagroChem),

AD-67 or MON 4660 (= 3-dichloroacetyl-1-oxa-3-aza-spiro [4,5] decan from Nitrokemia or Monsanto),

130/289

TI-35 (= TRI-Chemical RT 1-dichloroacetylazepano), diclonone (dicyclonone) or BAS145138 or LAB145138 (= 3-dichloro-acetyl2,5,5-trimethyl-1,3-diazabicyclo [4.3.0] nonane from BASF ) and

Furilazole or MON 13900 (see Pestic. Man.) (= (RS) -3-dichloroacetyl-5- (2-furyl) 2,2-dimethyloxazolidine).

[286] D) N-Acylsulfonamides of structural formula (S-IV) and their salts

R ^{1 r} 'D

O

(S-IV) in which the symbol Rd ¹ represents hydrogen, a hydrocarbon radical, a hydrocarbonoxy radical, a thiohydrocarbon radical or a heterocyclyl radical, which is preferably linked via a carbon atom, where each of the last 4 referred radicals is unsubstituted or is substituted with one or more radicals, the same or different, selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, carboxyl, formyl, carbonamide, sulfonamide and radicals of the general formula -Z ^to - R ^a , wherein each hydrocarbon residue preferably has 1 to 20 carbon atoms and a carbon containing Rd ¹ radical, including substituents, preferably has 1 to 30 carbon atoms;

the symbol Rd ² represents hydrogen or (C 1 -C 4) alkyl and preferably hydrogen or the symbols Rd ¹ and Rd ² , together with the group of general formula -CO-N-, constitute the radical of a saturated ring or unsaturated with 3 to 8 members; the symbols Rd ³ are the same or different and represent halogen, cyano, nitro, amino, hydroxyl, carboxyl, formyl, CONH2, SO2NH2 or a radical of the general formula -Z ^b -R ^b ;

Rd ⁴ represents hydrogen or (C 1 -C 4) alkyl and preferably H;

131/289 the Rd ⁵ symbols are the same or different and represent halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH2, SO2NH2 or a radical of the general formula -Z ^c -R ^c ;

the symbol R ^a represents a hydrocarbon radical or a heterocyclyl radical, in which each of the last two radicals referred to is unsubstituted or substituted with or more radicals, the same or different, selected from the group consisting of halogen, cyano, nitro, amino , hydroxyl, mono- and di [(C1 -C4 alkyl)] - amino, or an alkyl radical with several, preferably 2 or 3, non-adjacent CH2 groups which are replaced, in each case, by an oxygen atom;

the symbols R ^b , R ^c are the same or different and represent a hydrocarbon radical or a heterocyclyl radical, where each of the last two radicals referred to is unsubstituted or is substituted with or more radicals, the same or different, selected from the group constituted by halogen, cyano, nitro, amino, hydroxyl, phosphoryl, halo-alkoxy (C1-C4), mono- and di- [C1 -C4 alkyl] amino, or an alkyl radical with several, preferably 2 or 3 , non-adjacent CH2 groups that are replaced, in each case, by an oxygen atom;

the symbol Z ^a represents a divalent group of the general formula -O-, -S-, -CO-, -CS, -CO-O-, -CO-S-, -O-CO-, -S-CO-, -SO-, -SO2-, -nr * -, -co-nr * -, -nr * -co-, SO2-NR * - or -NR * -SO2-, where the link indicated on the right side of the group divalent in question is the bond to the radical R ^a and in which each of the symbols R *, in the last 5 radicals mentioned, independently represents H, alkyl (C1-C4) or haloalkyl (C1-C4) ;

the symbols Z ^b , Z ^c independently represent a direct bond or a divalent group of the general formula -O-, -S-, -CO-, -CS-, -CO-O-, -COS -, -O-CO-, -S-CO-, -SO-, -SO2-, -NR * -, -SO2-NR * -, -NR * -SO2-, -CO-NR * - or NR * -CO-, where the link indicated on the right side of the divalent group in question is a link to the radical R ^b or R ^c and where each of the symbols R *, in the last 5 referred radicals, represents, independently of each other , H,

132/289 (C 1 -C 4) alkyl or (C 1 -C 4) haloalkyl;

the symbol nD represents an integer between 0 and 4, preferably 0, 1 or 2 and more preferably 0 or 1 and the symbol mD represents an integer between 0 and 5, preferably 0, 1,2 or 3 and, in particular 0, 1 or 2.

[287] E) Acylsulfamoylbenzamides of structural formula (S-V), if appropriate also in the form of a salt,

O

R _e

Y-I

Re ⁴

X

E (RE ⁵ ) mE (SV) and the symbol Xe represents CH or N, the symbol Re ¹ represents hydrogen, heterocyclyl or a hydrocarbon radical, in which the last two radicals referred to are optionally substituted with one or more radicals, equal to or different, selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH2, SO2NH2 and Z ^a -R ^a ;

Re ² represents hydrogen, hydroxy, alkyl (C1-C6), alkenyl (C2-C6), alkynyl (C2-C6), alkoxy (C1-C6), alkenyl (C2-C6), where the last five radicals referred to are optionally substituted with one or more radicals, the same or different, selected from the group consisting of halogen, hydroxy, alkyl (C-C4), alkoxy (C-C4) and alkyl (C-C4) -tio or the symbols Re ¹ and Re ² , together with the nitrogen atom that supports them, form a saturated or unsaturated ring with 3 to 8 members; Re ³ represents halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH2, SO2NH2 or Z ^b -R ^b ;

Re ⁴ represents hydrogen, (C-C4) alkyl, alkenyl (C2-C4) or alkynyl (C2-C4);

the Re ⁵ symbol represents halogen, cyan, nitro, amino, hydroxyl, carboxyl,

Phosphoryl, CHO, CONH2, SO2NH2 or Z ^c -R ^c ;

the symbol R ^a represents an alkyl radical (C2-C2o), the carbon chain of which is interrupted once or more than once by oxygen atoms, represents heterocyclyl or a hydrocarbon radical, in which the last two radicals referred to are optionally substituted with one or more radicals, the same or different, selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, mono- and di- [(C-C4) alkyl] - amino;

the symbols R ^b , R ^c are the same or different and represent an alkyl radical (C2C20), the carbon chain of which is interrupted once or more than once by oxygen atoms, represent heterocyclyl or a hydrocarbon radical, where the two the latter radicals referred to are optionally substituted with one or more radicals, the same or different, selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, phosphoryl, haloalkoxy (C1C4), mono- and di- [C1 -C4 alkyl )] - amino;

the symbol Z ^a represents a divalent unit selected from the set consisting of O, S, CO, CS, C (O) O, C (O) S, SO, SO2, NR ^d , C (O) NR ^d and SO2NR ^d ; the symbols Z ^b , Z ^c are the same or different and represent a direct link or a divalent unit selected from the group consisting of O, S, CO, CS, C (O) O, C (O) S, SO, SO2, NR ^d , SO2NR ^d and C (O) NR ^d ;

R ^d represents hydrogen, (C 1 -C 4) alkyl or halo (C 1 -C 4) alkyl; the symbol nE represents an integer between 0 and 4 and the symbol mE, if the symbol X represents CH, it represents an integer between 0 and 5, and, if the symbol X represents N, it represents an integer between 0 and 4;

among these, compounds (also in the form of their salts) of the acylsulfamoylbenzamides type, for example, of the following structural formula (S-VI), which are known, for example, from WO 99/16744,

134/289

Η

(R _and ⁵ ),

Ε 'mE (S-VI)

Re ¹ = cyclopropyl and Re ⁵ = 2-OMe (cyprosulfamide, S3-1),

Re ¹ = cyclorpropyl and Re ⁵ = 5-CI-2-OMe (S3-2),

Re ¹ = ethyl and Re ⁵ = 2-OMe (S3-3),

Re ¹ = isopropyl and Re ⁵ = 5-CI-2-OMe (S3-4) and

Re ¹ = isopropyl and Re ⁵ = 2-OMe (S3-5).

[288] F) N-acylsulfamoylphenylurea compounds of structural formula (SVII), which are known, for example, from EP-A-365484

Rc

R _c

(S-VII) in which the symbol A represents a radical of the group consisting of

R ”

* 0R ^c

R ^{d Rt} Óor the symbols Rf ¹ and Rf ² , independently of each other, represent hydrogen, alkyl (C-C8), cycloalkyl (C3-C8), alkenyl (C3-C6), alkynyl (C3-C6) , or by (C1 -C4) alkoxy or

135/289

R ^x

- RY substituted alkoxy (C1-C4) or the symbols Rf ¹ and Rf ² together form an alkylene bridge (C4-C6) and an alkylene bridge (C4-C6) interrupted by oxygen, sulfur, SO, SO2, NH or N ((C1-C4) alkyl) -, the symbol Rf ³ represents hydrogen or (C1-C4) alkyl, the symbols Rf ⁴ and Rf ⁵ represent, independently of each other, hydrogen, halogen, cyano, nitro, trifluoromethyl, (C-C4) alkyl, (C-C4) alkoxy, (C-C4) alkyl, thio, (C-C4) alkylsulfinyl, (C-C4) alkylsulfonyl, -COORJ, CONR ^k R ^m , -COR ⁿ , -SO2NR ^k R ^m or -OSO2-alkyl (C1-C4), or the symbols R ^a and R ^b together form an alkylene bridge (C3-C4) that can be interrupted by halogen or alkyl (C1-C4) or an alkenylene (C3-C4) bridge that can be interrupted by halogen or alkyl (C1-C4) or a C4 alkenylene bridge that can be replaced with halogen or alkyl (C1-C4) and the symbols R ^g and R ^h independently represent hydrogen, halogen, (C-C4) alkyl, trifluorom ethyl, methoxy, methylthio or -COORJ, where the symbol R ^c represents hydrogen, halogen, alkyl (C1-C4) or methoxy, the symbol R ^d represents hydrogen, halogen, nitro, alkyl (C1-C4), alkoxy (CiC4 ), (C1-C4) alkylthio, (C1-C4) alkylsulfinyl, (C1-C4) alkylsulfonyl, -COORJ or CONR ^k R ^m , the symbol R ^and represents hydrogen, halogen, (C1-6) alkyl C4), -COORJ, trifluoromethyl or methoxy or the symbols R ^d and R ^and together form an alkylene bridge (C3-C4), the symbol R ^f represents hydrogen, halogen or alkyl (C-C4), the symbols R ^x and R ^Y independently represent hydrogen, halogen, alkyl (C1-C4), alkoxy (C1-C4), alkyl (C1-C4) -thio, -COOR ⁴ , trifluoromethyl, nitro or cyano, the symbols RJ, R ^k and R ^m represent, independently of each other,

136/289 hydrogen or (C1-C4) alkyl, the symbols R ^k and R ^m together form an alkylene bridge (C4-C6) or an alkylene bridge (C4-C6) interrupted by oxygen, NH or -N ( alkyl (C1-C4)) - and the symbol R ⁿ represents alkyl (C1-C4), phenyl or phenyl substituted with halogen, alkyl (C1-C4), methoxy, nitro or trifluoromethyl, among these are preferred:

- [4- (N-2-methoxybenzoylsulfamoyl) -phenyl] -3-methylurea, 1 - [4- (N-2-methoxybenzoylsulfamoyl) -phenyl] -3,3-dimethylurea, 1- [4- (N-4 , 5-dimethylbenzoylsulfamoyl) -phenyl] -3methyl-urea, 1- [4- (N-naphthylsulfamoyl) -phenyl] -3,3-dimethylurea, including stereoisomers and salts customary in agriculture.

G) Active compounds of the hydroxyaromatic and aromatic-aliphatic carboxylic acid derivative class, for example, ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylic acid, 1,2-dihydro-2-oxo-6trifluoromethylpyridine-3-carboxamide, 2-hydroxy-cinnamic acid, 2,4-dichlorokinamic acid, as described in WO 2004084631, WO 2005015994, WO 2006007981, WO 2005016001.

[289] H) Active compounds of the 1,2-dihydroquinoxaline-2-one class, for example, 1-methyl-3- (2-thienyl) -1,2-dihydroquinoxaline-2-one, 1 -methyl-3- (2-thienyl) 1,2-dihydroquinoxaline-2-thione, 1- (2-aminoethyl) -3- (2-thienyl) -1,2-dihydro-quinoxaline-2- hydrochloride one, 1- (2-methylsulfonylaminoethyl) -3- (2-thienyl) -1,2-dihydroquinoxaline-2-one, as described in WO 2005112630.

(a) Active compounds which, in addition to a herbicidal action against harmful plants, also have a phytoprotective action on crop plants, such as rice, such as, for example, dimepiperate or MY-93 (see Pestic. Man.) (= S1-methyl-1-phenylethyl piperidine-1-thiocarboxylate), which is known as a firoprotective agent for rice against damage caused by the herbicide molinate, daimurone or SK 23 (see Pestic. Man.) (= 1- (1-methyl-1-phenylethyl) -3-p-tolyl-urea), which is known as a phyroprotective agent for rice against damage

137/289 caused by the herbicide imazosulfurone, cumilurone = JC-940 (= 3- (2-chlorophenylmethyl) -1- (1-methyl-1-phenylethyl) -urea, see document JP-A-60087254), which is known as a phytoprotective agent for rice against damage caused by some herbicides, methoxyphenone or NK 049 (= 3,3'-dimethyl-4-methoxybenzophenone), which is known as a phytoprotective agent for rice against damage caused by some herbicides,

CSB (= 1-bromo-4- (chloromethylsulfonyl) -benzene) (CAS reg. No. 54091-06-4 from Kumiai), which is known as a phytoprotective agent for rice against damage caused by some herbicides.

[290] K) Compounds of structural formula (S-IX), as described in WO-A-1998/38856,

(S-IX) in which the symbols and indices have the following meanings:

the symbols Rk ¹ , Rk ² independently represent halogen, alkyl (C1-C4), alkoxy (C1-C4), haloalkyl (C1-C4), alkyl (C1-C4) -amino, di- (C 1 -C 4) alkylamino, nitro;

the symbol Ak represents COORk ³ or COORk ⁴ the symbols Rk ³ , Rk ⁴ independently represent hydrogen, (C-C4) alkyl, alkenyl (C2-C6), alkynyl (C2-C4), cyanoalkyl, haloalkyl (C1 -C4), phenyl, nitrophenyl, benzyl, halobenzyl, pyridinylalkyl and alkylammonium, the symbol nK ¹ represents 0 or 1 and the symbols nK ² , nK ³ independently represent between yes 0, 1 or 2;

preferably:

138/289 (a) (diphenylmethoxy) -methyl acetate (CAS reg. No .: 41858-19-9).

[291] L) Compounds of structural formula (S-X), as described in WO A-98/27049

(SX) in which the symbols and indices have the following meanings: the symbol Xl represents CH or N, the symbol nL, if X = N, represents an integer between 0 and 4 and in the case of X = CH, it represents a number integer between 0 and 5, the symbol R1 ¹ represents halogen, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C10-C4), haloalkoxy (C1-C4), nitro, alkyl (C1-C4) -io , (C1 -C4) alkylsulfonyl, (C1C4) alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy, R1 ² represents hydrogen or (C1-C4) alkyl, R1 ³ represents hydrogen, C1-4 alkyl Ce), alkenyl (Ci-C4), alkynyl (Ci15 C4) or aryl, in which each of the aforementioned carbon-containing radicals is unsubstituted or substituted with one or more, preferably with up to three, the same or different radicals selected from the group consisting of halogen and alkoxy; or their salts.

[292] M) Active compounds of the class of 3- (5-tetrazolylcarbonyl) -2-quinolones, eg 1,2-dihydro-4-hydroxy-1-ethyl-3- (5-tetrazolylcarbonyl) -2 -quinolone (CAS No.: 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3- (5tetrazolylcarbonyl) -2-quinolone (CAS No.: 95855-00-8), as described in WO-A-1999000020.

[293] N) Compounds of structural formula (S-XI) or (S-XII), as described in WO-A-2007023719 and WO-A-2007023764

139/289

N

N where Rn ¹ represents halogen, (C1 -C4) alkyl, methoxy, nitro, cyano, CF3,

OCF3, the symbols Y, Z independently represent O or S, the symbol nN represents an integer between 0 and 4, the symbol Rn ² represents alkyl (Ci-Cie), alkenyl (C2-C6) , (C3-C6) cycloalkyl, aryl; benzyl, halobenzyl, the symbol Rn ³ represents hydrogen, alkyl (Ci-Ce).

[294] O) One or more compounds in the group consisting of:

1,8-naphthalic anhydride, O phosphorodithioate, O-diethyl-S-2-ethylthioethyl (disulfotone), 4-chlorophenyl methylcarbamate (mefenate), O phosphorothioate, O-diethyl-O-phenyl (diethylate), 4 acid -carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic (CL304415, CAS reg .: 31541-57-8), 1-oxa-4-azaspiro [4.5] decane-4 -2-propenyl carbodithioate (MG-838, CAS no .: 133993-74-5), [(3-oxo-1H-2benzothiopyran-4 (3H) -ylidene) -methoxy] -methyl acetate ( from WOA98 / 13361; CAS reg .: 205121-04-6), cyanomethoxy-imino- (phenyl) acetonitrile (ciometrinyl), 1,3-dioxolane-2-ylmethoxy-imino- (phenyl) - 4'-chloro-2,2,2trifluoroacetophenone acetonitrile (oxabetrinyl), 4'-chloro-2,2,2trifluoroacetophenone (fluxophenim), 4,6-dichloro-2-phenylpyrimidine (phenclorin), 2chloro-4-trifluoromethyl- Benzyl 1,3-thiazole-5-carboxylate (flurazole), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), including the possible stereoisomers in each case, and including conventional agricultural salts.

[295] The weight ratios between herbicide (mixture) and phytoprotective agent generally depend on the rate of application of the herbicide and the effectiveness of the phytoprotective agent in question and can vary over wide limits, for example.

140/289 example, in the range comprised between 200: 1 and 1: 200, preferably between 100: 1 and 1: 100 and, in particular, between 20: 1 and 1:20. In an analogous way to compounds (I) or mixtures thereof, phytoprotective agents can be formulated with other herbicides / pesticides and can be presented and used as a finished formulation or as a tank mixture with the herbicides.

[296] For application, herbicide or herbicide / phytoprotective agent formulations present in a commercial form are, if appropriate, diluted in a conventional manner, for example, in the case of wettable powders, emulsifiable concentrates, dispersions and dispersible granules in water, with water. Preparations in the form of powders, granules for application to the soil or granules for spreading and sprayable solutions are normally not yet diluted with other inert substances before application.

[297] The required application rate of the compounds of structural formula (I), and / or their salts, varies according to external conditions, such as, inter alia, temperature, humidity and type of herbicide used. It may vary over extended intervals. For the application of herbicide to control harmful plants, it is, for example, between 0.001 and 10.0 kg / ha or more of active substance, preferably between 0.005 and 5 kg / ha and, in particular, between 0 , 01 and 1 kg / ha of active substance. This applies to pre-emergence and post-emergence application.

[298] When used as a plant growth regulator, for example, as a stem stabilizer for crop plants such as those mentioned above, preferably cereal plants such as wheat, barley, rye, triticale, millet, rice or maize, the application rate, for example, is between 0.001 and 2 kg / ha or more of active substance, preferably between 0.005 and 1 kg / ha, in particular, it is between 10 and 500 g / ha of active substance and more particularly it is comprised between 20 and 250 g / ha of active substance. (Please check if this should be noted). This applies to the pre-emergence method and the post-emergency method, and the post-emergency method is normally preferred.

[299] The application as a stalk stabilizer takes place in several stages of plant growth. For example, application after the tapering phase, at the beginning of longitudinal growth, is preferred.

[300] As an alternative, application as a plant growth regulator is also possible through seed treatment, which comprises several techniques for seed coating. In this case, the application rate depends on the particular techniques and can be determined in preliminary tests.

[301] By way of example, some examples of synthesis of compounds of formula (I) are described below. In the examples, quantities (including percentages) refer to weight, unless otherwise specified.

[302] The symbols> and <designate "greater than" and "less than", respectively. The symbol> designates “greater than or equal to, the symbol <designates less than or equal to.

[303] If, in the context of the description and examples, the terms R and S are assigned to the absolute configuration in a chirality scepter of the stereoisomers of structural formula (I), this nomenclature RS follows, unless defined differently, the Cahn-Ingold-Prelog rule.

(A) Examples of synthesis [304] Example A1: preparation of a mixture of erythro / threus diastereomers of

5- (2,6-dioxocyclohexyl) -2- (3-fluorophenyl) -3- (4-fluorophenyl) -5-oxopentanonitrile [table 2, example Iaa20]

Step 1: Methyl 4-cyano-4- (3-fluorophenyl) -3- (4-fluorophenyl) -butanoate [305] Under a protective gas (Ar) atmosphere, 0.767 g (5.0 mmol) was added of (3-fluorophenyl) -acetonitrile and 0.1 ml of a solution of sodium methoxide (30% in methanol) to 0.820 g (4.55 mmol) of methyl 3- (4-fluorophenyl) -acrylate in 15 , 0 ml of toluene and the mixture was stirred in a closed vessel at 65 ° C for 15 hours. The solvent was removed under reduced pressure, the residue was taken up

142/289 in ethyl acetate and the mixture was washed twice with 25 ml of water in each case. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was subjected to chromatography on silica gel (ethyl acetate / heptane = 20:80) to obtain 0.950 g (57% theoretical) of 4-cyano-4- (3-fluorophenyl) -3- (4 diastereomeric methyl fluorophenyl) butanoate (erythro: treo = 54:46, according to the integration of the methyl singlets in the ¹ H-NMR in CDCb at 3.66 and 3.56 ppm). Step 2: 4-cyano-3- (4-fluorophenyl) -4- (3-fluorophenyl) -butanoic acid [306] Under a protective gas (Ar) atmosphere, 10 mL of a 2 molar aqueous solution of sodium hydroxide to 1.75 g (5.55 mmol) of methyl 4-cyano4- (3-fluorophenyl) -3- (4-fluorophenyl) -butanoate in 50.0 ml of methanol and the mixture was stirred at 25 ° C for 8 hours. Methanol was removed under reduced pressure. The residue was acidified with concentrated hydrochloric acid (pH = 3) and extracted three times with 15 ml of dichloromethane in each case. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. 1.62 g (96.9% theoretical) of the title compound was obtained in the form of colorless crystals (erythro: treo = 49:51, comparison of multiplets in ¹ H-NMR in CDCb at 2.60 and 2, 85 ppm).

Step 3: 3-Oxocycle-hex1-ene-1-yl 4-cyano-4- (3-fluorophenyl) -3- (4-fluorophenyl) -butanoate [307] 1.79 g (15 mmol) was added of thionyl chloride to 0.452 g (1.5 mmol) of 4-cyano-3- (4-fluorophenyl) -4- (3-fluorophenyl) -butanoic acid and the mixture was stirred at 80 ° C for 1.5 hours. The excess thionyl chloride was removed under reduced pressure. The concentrated reaction mixture was thus dissolved (which contains acid chloride) in 3 ml of dichloromethane and, at 0 ° C, was added dropwise (about 30 minutes) to a mixture of 0.252 g (2.25 mmol) of 1,3-cyclohexanedione and 0.304 g (3 mmol) of triethylamine in dichloromethane (10 mL). After stirring for 3 hours at 25 ° C, the solvent was removed under reduced pressure, the residue was taken up in ethyl acetate and the mixture was washed twice with 25 ml of water in each case. The phases were dried

143/289 combined on sodium sulfate and the solvent was removed under reduced pressure.

[308] The resulting crude product in step 4 was reacted again.

Step 4: 5- (2,6-dioxocyclohexyl) -2- (3-fluorophenyl) -3- (4-fluorophenyl) -5-oxopentanonitrile [309] 0.013 g (0.15 mmol) of acetocyan was added -hydrin and 0.273 g (2.0 mmol) of triethylamine to 0.593 g (1.50 mmol) of 4-cyano-4- (3-fluorophenyl) -3- (4-fluorophenyl) -butanoate of 3-oxocyclo-hex-1 -eno-1-yl in 5.0 ml of acetonitrile and the mixture was stirred in a closed vessel at 25 ° C overnight. The solvent was removed under reduced pressure, the residue was taken up in ethyl acetate and the mixture was washed twice with 25 ml of water in each case. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. Preparative chromatography [(90 ml / minute acetonitrile / water (0.05% trifluoroacetic acid)] in a solid phase [Nucleodur C18, HTec C18 column, 10 pm, (250 x 50) -mm] was performed for obtain 0.267 g (45% theoretical) of a 5- (2,6-dioxocyclohexyl) -2- (3-fluorophenyl) -3- (4-fluorophenyl) -5-oxopentanonitrile diastereomer (erythro: threo) = 63:37, according to the integration of doublets in the ¹ H-NMR in CDCb at 4.30 ppm and 4.03 ppm);

¹ H-NMR on CDCb;

erythro: 17.47 (s, 1H), 4.30 (d, 1H), threus: 17.46 (s, 1H), 4.03 (d, 1H);

mass spectrum: molecular peak 394 [M-1] +;

HPLC retention time: 1.58 minutes.

[310] Example A2: mixture of 2- [3 (4-chlorophenyl) -4-cyano-4- (3-fluorophenyl) -butanoyl] -3-oxocyclohex-1-ene 2,2-dimethylpropanoate diastereomers -1-yl [table 2, example Iaa32] [311] 0.091 g (0.656 mmol) of triethylamine and, at 0 ° C, 0.069 g (0.568 mmol) of 2,2-dimethylpropanoyl chloride at 0.180 g ( 0.43 mmol) of 5- (2,6dioxocyclohexyl) -2- (3-fluorophenyl) -3- (4-chlorophenyl) -5-oxopentanonitrile in 3.0 ml of dichloromethane and the mixture was stirred in a vessel closed at 25 ° C for

144/289 hours. The solvent was removed under reduced pressure, the residue was taken up in ethyl acetate and the mixture was washed twice with 25 ml of water in each case. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. Preparative chromatography [(90 ml / minute acetonitrile / water (0.05% trifluoroacetic acid)] in a solid phase [Nucleodur C18, HTec C18 column, 10 pm, (250 x 50) -mm] was performed for obtain 114 mg (8% theoretical) of a mixture of erythro / threus diastereomers of

2- [3- (4-chlorophenyl) -4-cyano-4- (3-fluorophenyl) -butanoyl] -3oxo-cyclohex-1-ene-1-yl 2,2-dimethylpropanoate (erythro: threo = 70:30, according to the integration of the tert-butyl singlets in ¹ H-NMR in CDCb at 1.15 ppm and 1.06 ppm).

[312] Example A3: mixture of 2,6-dicyano-6- (3-fluorophenyl) -5 (4-fluorophenyl) -3-oxo-hexanoate diastereomers [table 26, example IB8aa1]

Step 1: Methyl 4-cyano-4- (3-fluorophenyl) -3- (4-fluorophenyl) -butanoate [313] Under a protective gas (Ar) atmosphere, 0.767 g (5.0 mmol) was added of (3-fluorophenyl) -acetonitrile and 0.1 ml of a solution of sodium methoxide (30% in methanol) to 0.820 g (4.55 mmol) of methyl 3- (4-fluorophenyl) -acrylate in 15 , 0 ml of toluene and the mixture was stirred in a closed vessel at 65 ° C for 15 hours. The solvent was removed under reduced pressure, the residue was taken up in ethyl acetate and the mixture was washed twice with 25 ml of water in each case. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel (ethyl acetate / heptane = 20:80) to obtain 0.950 g (57% theoretical) of a mixture of 4 cyano- (3-fluorophenyl) - erythro / threus diastereomers - Methyl 3- (4-fluorophenyl) -butanoate (erythro: threo = 54:46, according to the integration of the methyl singlets in the ¹ H-NMR in CDCb at 3.66 and 3.56 ppm).

Step 2: 4-cyano-3- (4-fluorophenyl) -4- (3-fluorophenyl) -butanoic acid [314] Under a protective gas (Ar) atmosphere, 10 mL of a 2 molar hydroxide solution was added sodium to 1.75 g (5.55 mmol) of methyl 4-cyano-3- (4-fluorophenyl) -4- (3-fluorophenyl) -butanoate (example A1) in 50.0 ml of

145/289 methanol and the mixture was stirred at 25 ° C for 8 hours. Methanol was removed under reduced pressure. The residue was acidified with concentrated hydrochloric acid (pH = 3) and extracted three times with 15 ml of dichloromethane in each case. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. 1.62 g (96.9% theoretical) of the title compound were obtained in the form of colorless crystals (erythro: treo = 49:51, according to the comparison of multiples in the ¹ H-NMR in CDCb at 2, 60 and 2.85 ppm).

Step 3: 2,6-dicyano-6- (3-fluorophenyl) -5- (4-fluorophenyl) -3-oxo-hexanoate [315] 1.79 g (20 mmol) of thionyl chloride was added to 0.603 g (2.0 mmol) of 4-cyano-3- (4-fluorophenyl) -4- (3-fluorophenyl) -butanoic acid and the mixture was stirred at 80 ° C for 1.5 hours. Excess thionyl chloride was removed under reduced pressure (residue = acid chloride). 0.297 g (3.00 mmol) of methyl cyanoacetate, 0.012 g (0.1 mmol) of 4-dimethylaminopyridine and the acid chloride dissolved in dichloromethane (5 mL) were added to 0.405 g (4.00 mmol) of triethylamine in 10 ml of dichloromethane and the mixture was stirred at 25 ° C for 2 hours. Then 50 ml of ethyl acetate was added and the mixture was extracted twice with 25 ml of water each time. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. Preparative chromatography [(90 ml / minute acetonitrile / water (0.05% trifluoroacetic acid)] in a solid phase [Nucleodur C18, HTec C18 column, 10 pm, (250 x 50) -mm] was performed for obtain 0.019 g (8% theoretical) of a 2,6-dicyano-6- (3-fluorophenyl) -5- (4-fluorophenyl) -3-oxo-hexanoate methyl erythro / threus mixture (erythro: 52 = 52 : 48, according to the integration of doublets in the ¹ H-NMR in CDCb at 4.09 ppm and 3.99 ppm).

[316] Example A4: methyl 2-acetyl-6-cyano-6- (3-fluorophenyl) -5- (4-fluorophenyl) -3-oxohexanoate diastereomers [table 27, example IBXaa20]

Step 1: Methyl 4-cyano-4- (3-fluorophenyl) -3- (4-fluorophenyl) -butanoate [317] Under a protective gas (Ar) atmosphere, 0.767 g (5.0 mmol) was added (3-fluorophenyl) -acetonitrile and 0.1 ml of sodium methoxide solution (at

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30% in methanol) to 0.820 g (4.55 mmol) of methyl 3- (4-fluorophenyl) -acrylate in 15.0 ml of toluene and the mixture was stirred in a closed vessel at 65 ° C for 15 hours. The solvent was removed under reduced pressure, the residue was taken up in ethyl acetate and the mixture was washed twice with 25 ml of water in each case. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel (ethyl acetate / heptane = 20:80) to obtain 0.950 g (57% theoretical) of a mixture of 4 cyano- (3-fluorophenyl) - erythro / threus diastereomers - Methyl 3- (4-fluorophenyl) -butanoate (erythro: threo = 54:46, according to integration of methyl singlets in ¹ H-NMR in CDCb at 3.66 and 3.56 ppm).

Step 2: 4-cyano-3- (4-fluorophenyl) -4- (3-fluorophenyl) -butanoic acid [318] Under a protective gas (Ar) atmosphere, 10 mL of a 2 molar aqueous solution of sodium hydroxide to 1.75 g (5.55 mmol) of methyl 4-cyano3- (4-fluorophenyl) -4- (3-fluorophenyl) -butanoate (example A1) in 50.0 ml of methanol and stirred the mixture at 25 ° C for 8 hours. Methanol was removed under reduced pressure. The residue was acidified with concentrated hydrochloric acid (pH = 3) and extracted three times with 15 ml of dichloromethane in each case. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. 1.62 g (96.9% theoretical) of the title compound were obtained in the form of colorless crystals (erythro: treo = 49:51, according to comparison of multiplets in the ¹ H-NMR in CDCb at 2.60 and 2.85 ppm).

Step 3: Methyl 2-acetyl-6-cyano-6- (3-fluorophenyl) -5- (4-fluorophenyl) -3-oxohexanoate [319] 2,379 g (20 mmol) of thionyl chloride were added to 0.603 g (2.0 mmol) of 4-cyano-3- (4-fluorophenyl) -4- (3-fluorophenyl) -butanoic acid and the mixture was stirred at 80 ° C for 1.5 hours. The excess thionyl chloride was removed under reduced pressure, providing the acid chloride as a residue. At 0 ° C, 0.316 g (4.00 mmol) of pyridine and then the acid chloride dissolved in dichloromethane (5 mL) were added to 0.190 g (2.00 mmol) of chloride

147/289 magnesium and 0.464 g (4.00 mmol) of methyl 3-oxobutanoate in dichloromethane (5 ml) and the mixture was stirred at 25 ° C for 1 hour. The residue was taken up in ethyl acetate and washed twice with 25 ml of water in each case. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. Preparative chromatography [(90 ml / minute acetonitrile / water (0.05% trifluoroacetic acid)] in a solid phase [Nucleodur C18, HTec C18 column, 10 pm, (250 x 50) -mm] was performed for obtain 0.422 g (52% theoretical) of the 2-acetyl-6-cyano-6- (3-fluorophenyl) -5- (4-fluorophenyl) -3-oxo-hexanoate methyl erythro / threo mixture (erythro: threo = 53:47, according to the integration of singlets in the ¹ H-NMR in CDCb at 17.74 ppm and 17.62 ppm).

[320] Example A5: 2- (3,4-difluorophenyl) -3- (3-fluorophenyl) -5- (5-methyl-1,2-oxazol-4yl) -5-oxopentanonitrile (see table 35, compound n ° IB10ga6)

Step 1: Methyl 4-cyano-4- (3,4-difluorophenyl) -3- (3-fluorophenyl) -butanoate [321] Under a protective gas (Ar) atmosphere, 3.828 g (25.0 (3,4-difluorophenyl) -acetonitrile and 0.281 mg of potassium tert-butoxide to 4.099 g (22.7 mmol) of methyl 3- (3-fluorophenyl) -acrylate in 25.0 ml of toluene and the mixture was stirred in a closed vessel at 65 ° C for 5 h. The solvent was removed under reduced pressure, the residue was taken up in ethyl acetate and the mixture was washed twice with 25 ml of water in each case. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel (ethyl acetate / heptane = 20:80) to obtain 7.3 g (87% theoretical) of 4-cyano-4- (3,4-difluorophenyl) - Diastereomeric methyl 3- (3-fluorophenyl) -butanoate (erythro: treo = 65:35, according to integration of the methyl singlets in the ¹ H-NMR in CDCb at 3.68 and 3.59 ppm).

Step 2: 4-cyano-4- (3,4-fluorophenyl) -3- (3-fluorophenyl) -butanoic acid [322] Under a protective gas (Ar) atmosphere, 23.5 ml of a solution was added aqueous 2 molar sodium hydroxide to 4.7 g (14.1 mmol) of 4-cyano-4 (3,4-difluorophenyl) -3- (3-fluorophenyl) -butanoate in 95.0 ml of methanol and

148/289 the mixture was stirred at 25 ° C overnight. Methanol was removed under reduced pressure. The residue was acidified with concentrated hydrochloric acid (pH = 3) and extracted three times with 100 ml of dichloromethane in each case. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. 4.50 g (99.9% theoretical) of the title compound were obtained in the form of colorless crystals (erythro: treo = 52:48, comparison of doublets in ¹ H-NMR in CDCb at 4.34 and 4, 04 ppm).

Step 3: 2- (3,4-difluorophenyl) -3- (3-fluorophenyl) -5- (5-methyl-1,2-oxazol-4-yl) -5oxopentanonitrile [323] In a dry and loaded Schlenk tube with argon, equipped with a magnetic stir bar and a partition, magnesium chips (291 mg, 11.9 mmol), zinc chloride (717 mg, 5.26 mmol) and lithium chloride (254 mg) were initially introduced , 5.98 mmol) in THF (5 ml) and activated by adding DIBAL-H (0.2 ml, 1 M in THF). After stirring for 5 minutes, 4-iodo-5-methyl-1,2-oxazole (1.0 g, 4.78 mmol) in anhydrous THF (3 mL) was added dropwise at 20 ° C . Then, the reaction mixture was stirred at 25 ° C for an additional 30 minutes. The resulting impure solution is then reacted with the acid chloride below.

[324] 6.84 g (57.5 mmol) of thionyl chloride were added to 1.83 g (5.75 mmol) of 4-cyano-4- (3,4-difluorophenyl) -3- ( 3-fluorophenyl) -butanoic and the mixture was stirred at 80 ° C for 1.5 hours. The excess thionyl chloride was removed under reduced pressure. The concentrated reaction mixture was thus dissolved (contains acid chloride) in 3 ml of dichloromethane and, at -10 ° C, was added dropwise (about 30 minutes) to the previous impure solution and then stirred at 25 ° C for an additional 2 hours. The solvent was removed under reduced pressure, the residue was taken up in ethyl acetate and the mixture was washed twice with 25 ml of water in each case. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel (ethyl acetate / heptane = 20:80) to obtain 810 mg (44% theoretical) of the mixture of 2- (3,4-difluorophenyl) -3- (3 -fluorophenyl) -5- (5-methyl-1,2-oxazol-4-yl) -5149/289 diastereomeric oxopentanonitrile (erythro: treo = 63:37, according to the integration of the methyl singlets in the ¹ H-NMR in CDCb at 8.54 and 8.48 ppm).

NMR (erythro): 8.54 (s, 1H), 7.22 (m, 1H), 7.09 (m, 1H), 6.98 (m, 2H), 6.82 (m, 3H), 4.51 (d, 1H), 3.71 (m, 1H), 3.50 (dd, 1H), 3.27 (dd, 1H), 2.75 (s, 3H);

MS: 385 [M + 1] +; HPLC (tr): 1.57 minutes [325] Example No. IB10ga6:

NMR (treo): 8.48 (s, 1H), 7.27 (m, 1H), 7.12 (m, 1H), 6.96 (m, 5H), 4.13 (d, 1H), 3.82 (m, 1H), 3.39 (dd, 1H), 3.23 (dd, 1H), 2.65 (s, 3H);

MS: 385 [M + 1] +; HPLC (tr): 1.57 minutes.

[326] The compounds described in the following tables are obtained according to the examples described above or in a similar way to this, if appropriate through the supplementary use of general methods described above. [327] In the following tables:

H = hydrogen (atom) Me = methyl or CH3 Et = ethyl n-Pr = n-propyl i-Pr = isopropyl n-Bu = n-butyl i-Bu = isobutyl tr = retention time F, Cl, Br, I fluorine, chlorine, bromine and iodine, respectively, in compliance with the chemical atomic symbol conventional MeO or OMe = methoxy CN = cyan NO2 = nitro Ph = phenyl

[328] The position of a substituent on the phenyl ring, for example, at position 2, is referred to as a prefix in the symbol or abbreviation of the radical, for example,

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2-Cl = 2-chlorine

2-Me = 2-methyl.

[329] Substitute position numbers for di- or tri-substituted substitution patterns are similarly referred to as prefixes, for example,

3,5-Me2 = 3,5-dimethyl (e.g., as a substitution on the phenyl ring)

2.3- Cl2 = 2,3-dichloro (e.g., as a substitution on the phenyl ring)

3.4- F2 = 3,4-difluoro (e.g., as a substitution on the phenyl ring) [330] Other abbreviations should be understood analogously to the examples 10 mentioned above.

(R ¹ ) m = H = unsubstituted cycle (m = 0) (R ² ) n = H = unsubstituted cycle (n = 0) [331] In addition, conventional chemical symbols and general formulas, such as such as, for example, CH2 for methylene or CF3 for trifluoromethyl or OH for hydroxyl. Correspondingly, compound meanings are defined as composed by the abbreviations referred to.

[332] Table 1: definitions of structural combinations of groups Q, (R ¹ ) m (R ² ) n, for the following tables of compounds of structural formula (I) according to the invention.

No. Q (R ¹ ) m (R ² ) n 1 OH 3-F 4-Cl 2 OH 3-F 3-F 3 OH 3,4-F2 4-Cl 4 OH 3-F 4-Br 5 OH 3-Cl 3-F 6 OH 3,4-F2 3-F 7 OH H 3-Br 8 OH 4-F 3-F 9 OH 3-F 3-Cl 10 OH 3,4-F2 3-Cl

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No. Q (R ¹ ) m (R ² ) n 11 OH 3-Br 3-F 12 OH 2.5-F2 3-F 13 OH 3-F 2-F 14 OH 3,4,5-Fa 4-Cl 15 OH 4-F 3-Cl 16 OH 3,4-F2 3-F, 4-Cl 17 OH 3,4-F2 2-F 18 OH 3-F 2,3-F2 19 OH 4-F 3,5-F2 20 OH 3-F 4-F 21 OH 3,4-F2 3-Cl, 5-F 22 OH 3-F 3-Cl, 5-F 23 OH 3-F 2.5-F2 24 OH 3,4-F2 2,3-F2 25 OH 3,4-F2 2.5-F2 26 OH 3-Cl 3-Cl, 5-F 27 OH 3-F, 4-Cl 3-Cl 28 OH 3,4-F2 3-NO2 29 OH 3,4-F2 H 30 OH 3-Cl, 4-F 3-F 31 OH 3,4-F2 4-OMe 32 O-C (O) -t-Bu 3-F 4-Cl 33 O-C (O) Me 3-F 4-Cl 34 SPh 3-F 4-Cl 35 SMe 3-F 4-Cl 36 OSO2 (4-Me-Ph) 3-F 4-Cl 37 Cl 3-F 4-Cl 38 O-CO2Me 3-F 4-Cl

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No. Q (R ¹ ) m (R ² ) n 39 O-C (O) -t-Bu 3-F 3-F 40 O-C (O) Me 3-F 3-F 41 SPh 3-F 3-F 42 SMe 3-F 3-F 43 OSO2 (4-Me-Ph) 3-F 3-F 44 Cl 3-F 3-F 45 O-CO2Me 3-F 3-F 46 O-C (O) -t-Bu 3,4-F2 3-F 47 O-C (O) Me 3,4-F2 3-F 48 O-C (O) Et 3,4-F2 3-F 49 SMe 3,4-F2 3-F 50 OSO2 (4-Me-Ph) 3,4-F2 3-F 51 Cl 3,4-F2 3-F 52 CO2Me 3,4-F2 3-F 53 O-C (O) -t-Bu 3,4-F2 3-Cl 54 O-C (O) Me 3,4-F2 3-Cl 55 SPh 3,4-F2 3-Cl 56 SMe 3,4-F2 3-Cl 57 OSO2 (4-Me-Ph) 3,4-F2 3-Cl 58 Cl 3,4-F2 3-Cl 59 O-CO2Me 3,4-F2 3-Cl 60 O-C (O) -t-Bu 3-Br 3-F 61 O-C (O) Me 2.5-F2 3-F 62 SPh 3-F 2-F 63 O-C (O) -t-Bu 3,4,5-Fa 4-Cl 64 O-C (O) Me 4-F 3-Cl 65 SPh 3,4-F2 3-F, 4-Cl 66 O-C (O) -t-Bu 3,4-F2 2-F

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No. Q (R ¹ ) m (R ² ) n 67 O-C (O) Me 3-F 2,3-F2 68 SPh 4-F 3,5-F2 69 O-C (O) -t-Bu 3-F 4-F 70 O-C (O) Me 3,4-F2 3-Cl, 5-F 71 SPh 3-F 3-Cl, 5-F 72 O-C (O) -t-Bu 3-F 2.5-F2 73 O-C (O) Me 3,4-F2 2,3-F2 74 SPh 3,4-F2 2.5-F2 75 O-C (O) -t-Bu 3-Cl 3-Cl, 5-F 76 O-C (O) Me 3-F, 4-Cl 3-Cl 77 SPh 3,4-F2 3-NO2 78 O-C (O) -t-Bu 3,4-F2 H 79 O-C (O) Me 3-Cl, 4-F 3-F 80 SPh 3,4-F2 4-OMe 81 OH 3-F H 82 OH 3-F 2,4-F2 83 OH 3-F 2,6-F2 84 OH 3-F 3,4-F2 85 OH 3-F 3,5-F2 86 OH 3-F 2-Cl 87 OH 3-F 2,3-Cl2 88 OH 3-F 2,4-Cl2 89 O-C (O) -t-Bu 3-F 2.5-Cl2 90 SPh 3-F 2,6-Cb 91 OH 3-F 3,4-Cl2 92 OH 3-F 3,5-Cl2 93 O-C (O) -t-Bu 3,4-F2 4-F 94 OH 3,4-F2 2,4-F2

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No. Q (R ¹ ) m (R ² ) n 95 OH 3,4-F2 2,6-F2 96 OH 3,4-F2 3,4-F2 97 OH 3,4-F2 3,5-F2 98 SPh 3,4-F2 2-Cl 99 O-C (O) -t-Bu 3,4-F2 2,3-Cb 100 OH 3,4-F2 2,4-Cb 101 O-C (O) -t-Bu 3,4-F2 2.5-Cb 102 OH 3,4-F2 2,6-Cb 103 SPh 3,4-F2 3,4-Cb 104 OH 3,4-F2 3-Br 105 OH 3-Cl 3-NO2 106 OH 3-Cl 4-NO2 107 OH 3-Cl 4-CN 108 OH 3-Cl 2-Br 109 O-C (O) -t-Bu 3-Cl 2,4-F2 110 OH 3-Br 2.5-F2 111 OH 3-Cl 2,6-F2 112 O-C (O) -t-Bu 3-Cl 3,4-F2 113 OH 3-Br 3,5-F2 114 OH 3-Cl 2-Cl 115 OH 3-Br 3-Cl 116 SPh 3-Cl 4-Cl 117 OH 3-Br 2,3-Cb 118 OH 3-Br 2,4-Cb 119 OH 3-Cl 2.5-Cb 120 SPh 3-Cl 2,6-Cb 121 SPh 3-Cl 3,4-Cb 122 OH 3-Cl 3.5-Cb

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No. Q (R ¹ ) m (R ² ) n 123 O-C (O) Me 3,4-Cb H 124 O-C (O) Me 3,4-Cb 2-F 125 O-C (O) Me 3,4-Cb 3-F 126 O-C (O) Me 3,4-Cb 4-F 127 O-C (O) Me 3,4-Cb 2,3-F2 128 O-C (O) Me 3,4-Cb 2,4-F2 129 OH 3,4-Cb 2.5-F2 130 O-C (O) Me 3,4-Cb 2,6-F2 131 O-C (O) -t-Bu 3,4-Cb 3,4-F2 132 O-C (O) Et 3,4-Cb 3,5-F2 133 O-C (O) Et 3,4-Cb 2-Cl 134 O-C (O) Et 3,4-Cb 3-Cl 135 O-C (O) -t-Bu 3,4-Cb 4-Cl 136 SPh 3,4-Cb 2,3-Cb 137 O-C (O) -t-Bu 3,4-Cb 2,4-Cb 138 O-C (O) Me 3,4-Cb 2.5-Cb 139 O-C (O) Et 3,4-Cb 2,6-Cb 140 O-C (O) Me 3,4-Cb 3,4-Cb 141 O-C (O) Me 3,4-Cb 3.5-Cb 142 O-C (O) Et 3-Cl, 4-F H 143 SMe 3-Cl, 4-F 2-F 144 O-C (O) Me 3-Cl, 4-F 4-F 145 O-C (O) Et 3-Cl, 4-F 2,3-F2 146 O-C (O) -t-Bu 3-Cl, 4-F 2,4-F2 147 O-C (O) Me 3-Cl, 4-F 2.5-F2 148 SPh 3-Cl, 4-F 2,6-F2 149 O-C (O) Et 3-Cl, 4-F 3,4-F2 150 OSO2 (4-Me-Ph) 3-Cl, 4-F 3,5-F2

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No. Q (R ¹ ) m (R ² ) n 151 O-C (O) Me 3-Cl, 4-F 2-Cl 152 OH 3-Cl, 4-F 3-Br 153 O-C (O) Me 3-Cl, 4-F 4-Cl 154 O-C (O) Me 3-Cl, 4-F 2,3-Cb 155 O-C (O) Et 3-Cl, 4-F 2,4-Cl2 156 O-C (O) Me 3-Cl, 4-F 2.5-Cb 157 O-C (O) Me 3-Cl, 4-F 2,6-Cb 158 O-C (O) Et 3-Cl, 4-F 3,4-Cb 159 O-C (O) Me 3-Cl, 4-F 3.5-Cb 160 O-C (O) Me 3-Cl, 4-F H 161 O-C (O) Et 3-F, 4-Cl 2-F 162 O-C (O) Me 3-F, 4-Cl 3-F 163 O-C (O) Me 3-F, 4-Cl 4-F 164 OH 3-F, 4-Cl 2,3-F2 165 O-C (O) Et 3-F, 4-Cl 2,4-F2 166 SPh 3-F, 4-Cl 2.5-F2 167 O-C (O) Me 3-F, 4-Cl 2,6-F2 168 O-C (O) Me 3-F, 4-Cl 3,4-F2 169 OH 3-F, 4-Cl 3,5-F2 170 O-C (O) Me 3-F, 4-Cl 2-Cl 171 O-C (O) Et 3-F, 4-Cl 4-Cl 172 SPh 3-F, 4-Cl 2,3-Cb 173 SPh 3-F, 4-Cl 2,4-Cb 174 SPh 3-F, 4-Cl 2.5-Cb 175 SPh 3-F, 4-Cl 2,6-Cb 176 SPh 3-F, 4-Cl 3,4-Cb 177 SPh 3-F, 4-Cl 3.5-Cb 178 O-C (O) -i-Pr 3-F 2,6-F2

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No. Q (R ¹ ) m (R ² ) n 179 O-C (O) Me 3-F 2,6-F2 180 SEt 3-F 2,6-F2 181 OH 3,4-F2 3,4-Cb 182 OH 3,4-F2 3.5-Cb 183 OH 3-Cl H 184 OH 3-Cl 2-F 185 OH 3-Cl 4-F 186 OH 3-Cl 2,3-F2 187 OH 3-Cl 2,4-F2 188 OH 3-Cl 2.5-F2 189 O-C (O) -t-Bu 3-Cl 2,6-F2 190 OH 3-Cl 3,4-F2 191 OH 3-Cl 3,5-F2 192 SPh 3-Cl 2-Cl 193 OH 3-Cl 3-Cl 194 OH 3-Cl 4-Cl 195 OH 3-Cl 2,3-Cb 196 OH 3-Cl 2,4-Cb 197 O-C (O) -t-Bu 3-Cl 2.5-Cb 198 OH 3-Cl 2,6-Cb 199 O-C (O) -t-Bu 3-Cl 3,4-Cb 200 O-C (O) Me 3-Cl 3.5-Cb 201 OH 3,4-Cb H 202 OH 3,4-Cb 2-F 203 OH 3,4-Cb 3-F 204 OH 3,4-Cb 4-F 205 O-C (O) -t-Bu 3,4-Cb 2,3-F2 206 O-C (O) Me 3,4-Cb 2,4-F2

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No. Q (R ¹ ) m (R ² ) n 207 SPh 3,4-Cb 2.5-F2 208 OH 3,4-Cb 2,6-F2 209 OSO2 (4-Me-Ph) 3,4-Cb 3,4-F2 210 OH 3,4-Cb 3,5-F2 211 OH 3,4-Cb 2-Cl 212 OH 3,4-Cb 3-Cl 213 OH 3,4-Cb 4-Cl 214 O-C (O) -t-Bu 3,4-Cb 2,3-Cb 215 OH 3,4-Cb 2,4-Cb 216 OH 3,4-Cb 2.5-Cb 217 OH 3,4-Cb 2,6-Cb 218 OH 3,4-Cb 3,4-Cb 219 OH 3,4-Cb 3.5-Cb 220 OH 3-Cl, 4-F H 221 OH 3-Cl, 4-F 2-F 222 OH 3-Cl, 4-F 4-F 223 OH 3-Cl, 4-F 2,3-F2 224 OH 3-Cl, 4-F 2,4-F2 225 OH 3-Cl, 4-F 2.5-F2 226 OH 3-Cl, 4-F 2,6-F2 227 OH 3-Cl, 4-F 3,4-F2 228 OH 3-Cl, 4-F 3,5-F2 229 OH 3-Cl, 4-F 2-Cl 230 OH 3-Cl, 4-F 3-Cl 231 OH 3-Cl, 4-F 4-Cl 232 OH 3-Cl, 4-F 2,3-Cb 233 OH 3-Cl, 4-F 2,4-Cb 234 OH 3-Cl, 4-F 2.5-Cb

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No. Q (R ¹ ) m (R ² ) n 235 OH 3-Cl, 4-F 2,6-Cl2 236 OH 3-Cl, 4-F 3,4-Cl2 237 OH 3-Cl, 4-F 3,5-Cl2 238 OH 3-Cl, 4-F H 239 OH 3-F, 4-Cl 2-F 240 OH 3-F, 4-Cl 3-F 241 OH 3-F, 4-Cl 4-F 242 SPh 3-F, 4-Cl 2,3-F2 243 OH 3-F, 4-Cl 2,4-F2 244 OH 3-F, 4-Cl 2.5-F2 245 OH 3-F, 4-Cl 2,6-F2 246 OH 3-F, 4-Cl 3,4-F2 247 OH 3-F, 4-Cl 3,5-F2 248 OH 3-F, 4-Cl 2-Cl 249 OH 3-F, 4-Cl 4-Cl 250 SPh 3-F, 4-Cl 2,3-Cl2 251 OH 3-F, 4-Cl 2,4-Cl2 252 OH 3-F, 4-Cl 2.5-Cl2 253 OH 3-F, 4-Cl 2,6-Cl2 254 OH 3-F, 4-Cl 3,4-Cl2 255 OH 3-F, 4-Cl 3,5-Cl2 256 SPh 3-F 2,6-F2 257 O-C (O) -t-Bu 3-F 2,6-F2 258 SMe 3-F 2,6-F2 259 O-C (O) Et 3,4-F2 2,6-F2 260 O-C (O) -t-Bu 3,4-F2 2,6-F2 261 O-C (O) Me 3,4-F2 2,6-F2 262 SPh 3,4-F2 2,6-F2

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No. Q (R ¹ ) m (R ² ) n 263 SMe 3,4-F2 2,6-F2 264 OSO2 (4-Me-Ph) 3,4-F2 2,6-F2 265 Cl 3,4-F2 2,6-F2 266 O-CO2Me 3,4-F2 2,6-F2 267 OH 3-CN H 268 OH 3-CN 2.5-F2 269 OH 3-CN 2,6-F2 270 OH 3-CN 2,3-F2 271 OH 3-CN 2,4-F2 272 OH 3-CN 3,4-F2 273 OH 3-CN 3,5-F2 274 OH 3-CN 4-Cl 275 OH 3-CN 3-Cl 276 OH 3-CN 2-Cl 277 OH 3-CN 4-F 278 OH 3-CN 3-F 279 OH 3-CN 2-F 280 OH 2-CN 3-F 281 OH 2-CN 4-F 282 OH 2-CN 4-Cl 283 OH 3-NO2 H 284 OH 3-NO2 2.5-F2 285 OH 3-NO2 2,6-F2 286 OH 3-NO2 2,3-F2 287 OH 3-NO2 2,4-F2 288 OH 3-NO2 3,4-F2 289 OH 3-NO2 3,5-F2 290 OH 3-NO2 4-Cl

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No. Q (R ¹ ) m (R ² ) n 291 OH 3-NO2 3-Cl 292 OH 3-NO2 2-Cl 293 OH 3-NO2 4-F 294 OH 3-NO2 3-F 295 OH 3-NO2 2-F 296 OH H 2,6-F2 297 OH H 3,4-F2 298 OH H 3,5-F2 299 OH H 2,3-F2 300 OH H 2,4-F2 301 OH H 2.5-F2 302 OH H 2-Cl 303 OH H 3-Cl 304 OH H 4-Cl 305 OH H 2-F 306 OH H 3-F 307 OH H 4-F 308 OH H 2,3-Cb 309 OH H 2,4-Cb 310 OH H 2.5-Cb 311 OH H 2,6-Cb 312 OH H 3,4-Cb 313 OH H 3.5-Cb 314 O-C (O) Et 3-CN 2.5-F2 315 O-C (O) -t-Bu 3-CN 2.5-F2 316 O-C (O) Me 3-CN 2.5-F2 317 SPh 3-CN 2.5-F2 318 SMe 3-CN 2.5-F2

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No. Q (R ¹ ) m (R ² ) n 319 OSO2 (4-Me-Ph) 3-CN 2.5-F2 320 Cl 3-CN 2.5-F2 321 O-CO2Me 3-CN 2.5-F2 322 O-C (O) Et 3-CN 2,6-F2 323 O-C (O) -t-Bu 3-CN 2,6-F2 324 O-C (O) Me 3-CN 2,6-F2 325 SPh 3-CN 2,6-F2 326 SMe 3-CN 2,6-F2 327 OSO2 (4-Me-Ph) 3-CN 2,6-F2 328 Cl 3-CN 2,6-F2 329 O-CO2Me 3-CN 2,6-F2 330 O-C (O) Et 3-CN 2,3-F2 331 O-C (O) -t-Bu 3-CN 2,3-F2 332 O-C (O) Me 3-CN 2,3-F2 333 SPh 3-CN 2,3-F2 334 SMe 3-CN 2,3-F2 335 OSO2 (4-Me-Ph) 3-CN 2,3-F2 336 Cl 3-CN 2,3-F2 337 O-CO2Me 3-CN 2,3-F2 338 O-C (O) Et 3-CN 2,4-F2 339 O-C (O) -t-Bu 3-CN 2,4-F2 340 O-C (O) Me 3-CN 2,4-F2 341 SPh 3-CN 2,4-F2 342 SMe 3-CN 2,4-F2 343 OSO2 (4-Me-Ph) 3-CN 2,4-F2 344 Cl 3-CN 2,4-F2 345 O-CO2Me 3-CN 2,4-F2 346 O-C (O) Et 3-CN 2,4-F2

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No. Q (R ¹ ) m (R ² ) n 347 O-C (O) -t-Bu 3-CN 2,4-F2 348 O-C (O) Me 3-CN 2,4-F2 349 SPh 3-CN 2,4-F2 350 SMe 3-CN 2,4-F2 351 OSO2 (4-Me-Ph) 3-CN 2,4-F2 352 Cl 3-CN 2,4-F2 353 O-CO2Me 3-CN 2,4-F2 354 O-C (O) Et 3-CN 4-Cl 355 O-C (O) -t-Bu 3-CN 4-Cl 356 O-C (O) Me 3-CN 4-Cl 357 SPh 3-CN 4-Cl 358 SMe 3-CN 4-Cl 359 OSO2 (4-Me-Ph) 3-CN 4-Cl 360 Cl 3-CN 4-Cl 361 O-CO2Me 3-CN 4-Cl 362 O-C (O) Et 3-CN 3-Cl 363 O-C (O) -t-Bu 3-CN 3-Cl 364 O-C (O) Me 3-CN 3-Cl 365 SPh 3-CN 3-Cl 366 SMe 3-CN 3-Cl 367 OSO2 (4-Me-Ph) 3-CN 3-Cl 368 Cl 3-CN 3-Cl 369 O-CO2Me 3-CN 3-Cl 370 O-C (O) Et 3-CN 4-F 371 O-C (O) -t-Bu 3-CN 4-F 372 O-C (O) Me 3-CN 4-F 373 SPh 3-CN 4-F 374 SMe 3-CN 4-F

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No. Q (R ¹ ) m (R ² ) n 375 OSO2 (4-Me-Ph) 3-CN 4-F 376 Cl 3-CN 4-F 377 O-CO2Me 3-CN 4-F 378 O-C (O) Et 3-CN 3-F 379 O-C (O) -t-Bu 3-CN 3-F 380 O-C (O) Me 3-CN 3-F 381 SPh 3-CN 3-F 382 SMe 3-CN 3-F 383 OSO2 (4-Me-Ph) 3-CN 3-F 384 Cl 3-CN 3-F 385 O-CO2Me 3-CN 3-F 386 O-C (O) Et 3-NO2 2.5-F2 387 O-C (O) -t-Bu 3-NO2 2.5-F2 388 O-C (O) Me 3-NO2 2.5-F2 389 SPh 3-NO2 2.5-F2 390 SMe 3-NO2 2.5-F2 391 OSO2 (4-Me-Ph) 3-NO2 2.5-F2 392 Cl 3-NO2 2.5-F2 393 O-CO2Me 3-NO2 2.5-F2 394 O-C (O) Et 3-NO2 2,6-F2 395 O-C (O) -t-Bu 3-NO2 2,6-F2 396 O-C (O) Me 3-NO2 2,6-F2 397 SPh 3-NO2 2,6-F2 398 SMe 3-NO2 2,6-F2 399 OSO2 (4-Me-Ph) 3-NO2 2,6-F2 400 Cl 3-NO2 2,6-F2 401 O-CO2Me 3-NO2 2,6-F2 402 O-C (O) Et 3-NO2 2,3-F2

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No. Q (R ¹ ) m (R ² ) n 403 O-C (O) -t-Bu 3-NO2 2,3-F2 404 O-C (O) Me 3-NO2 2,3-F2 405 SPh 3-NO2 2,3-F2 406 SMe 3-NO2 2,3-F2 407 OSO2 (4-Me-Ph) 3-NO2 2,3-F2 408 Cl 3-NO2 2,3-F2 409 O-CO2Me 3-NO2 2,3-F2 410 O-C (O) Et 3-NO2 2,4-F2 411 O-C (O) -t-Bu 3-NO2 2,4-F2 412 O-C (O) Me 3-NO2 2,4-F2 413 SPh 3-NO2 2,4-F2 414 SMe 3-NO2 2,4-F2 415 OSO2 (4-Me-Ph) 3-NO2 2,4-F2 416 Cl 3-NO2 2,4-F2 417 O-CO2Me 3-NO2 2,4-F2 418 O-C (O) Et 3-NO2 2,4-F2 419 O-C (O) -t-Bu 3-NO2 2,4-F2 420 O-C (O) Me 3-NO2 2,4-F2 421 SPh 3-NO2 2,4-F2 422 SMe 3-NO2 2,4-F2 423 OSO2 (4-Me-Ph) 3-NO2 2,4-F2 424 Cl 3-NO2 2,4-F2 425 O-CO2Me 3-NO2 2,4-F2 426 O-C (O) Et 3-NO2 4-Cl 427 O-C (O) -t-Bu 3-NO2 4-Cl 428 O-C (O) Me 3-NO2 4-Cl 429 SPh 3-NO2 4-Cl 430 SMe 3-NO2 4-Cl

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No. Q (R ¹ ) m (R ² ) n 431 OSO2 (4-Me-Ph) 3-NO2 4-Cl 432 Cl 3-NO2 4-Cl 433 O-CO2Me 3-NO2 4-Cl 434 O-C (O) Et 3-NO2 3-Cl 435 O-C (O) -t-Bu 3-NO2 3-Cl 436 O-C (O) Me 3-NO2 3-Cl 437 SPh 3-NO2 3-Cl 438 SMe 3-NO2 3-Cl 439 OSO2 (4-Me-Ph) 3-NO2 3-Cl 440 Cl 3-NO2 3-Cl 441 O-CO2Me 3-NO2 3-Cl 442 O-C (O) Et 3-NO2 4-F 443 O-C (O) -t-Bu 3-NO2 4-F 444 O-C (O) Me 3-NO2 4-F 445 SPh 3-NO2 4-F 446 SMe 3-NO2 4-F 447 OSO2 (4-Me-Ph) 3-NO2 4-F 448 Cl 3-NO2 4-F 449 O-CO2Me 3-NO2 4-F 450 O-C (O) Et 3-NO2 3-F 451 O-C (O) -t-Bu 3-NO2 3-F 452 O-C (O) Me 3-NO2 3-F 453 SPh 3-NO2 3-F 454 SMe 3-NO2 3-F 455 OSO2 (4-Me-Ph) 3-NO2 3-F 456 Cl 3-NO2 3-F 457 O-CO2Me 3-NO2 3-F 458 Me 3-CN, 4-F 3-F

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No. Q (R ¹ ) m (R ² ) n 459 Me 3-CN, 4-F 3-Cl 460 Me 3-CN, 4-F 3-CN 461 Me 3-CN, 4-F 4-F 462 Me 3-CN, 4-F 4-Cl 463 Me 3-CN, 4-F 2.5-F2 464 Me 3-CN, 4-F 2,6-F2 465 H 3-CN, 4-F 3-F 466 H 3-CN, 4-F 3-Cl 467 H 3-CN, 4-F 3-CN 468 H 3-CN, 4-F 4-F 469 H 3-CN, 4-F 4-Cl 470 H 3-CN, 4-F 2.5-F2 471 H 3-CN, 4-F 2,6-F2 472 Me 3-Br, 4-F 3-F 473 Me 3-Br, 4-F 3-Cl 474 Me 3-Br, 4-F 3-CN 475 Me 3-Br, 4-F 4-F 476 Me 3-Br, 4-F 4-Cl 477 Me 3-Br, 4-F 2.5-F2 478 Me 3-Br, 4-F 2,6-F2 479 H 3-Br, 4-F 3-F 480 H 3-Br, 4-F 3-Cl 481 H 3-Br, 4-F 3-CN 482 H 3-Br, 4-F 4-F 483 H 3-Br, 4-F 4-Cl 484 H 3-Br, 4-F 2.5-F2 485 H 3-Br, 4-F 2,6-F2 486 Me 3-F, 4-CN 3-F

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No. Q (R ¹ ) m (R ² ) n 487 Me 3-F, 4-CN 3-Cl 488 Me 3-F, 4-CN 3-CN 489 Me 3-F, 4-CN 4-F 490 Me 3-F, 4-CN 4-Cl 491 Me 3-F, 4-CN 2.5-F2 492 Me 3-F, 4-CN 2,6-F2 493 H 3-F, 4-CN 3-F 494 H 3-F, 4-CN 3-Cl 495 H 3-F, 4-CN 3-CN 496 H 3-F, 4-CN 4-F 497 H 3-F, 4-CN 4-Cl 498 H 3-F, 4-CN 2.5-F2 499 H 3-F, 4-CN 2,6-F2 [333] Del definitions of the examples in Tables 2 to 24f below

[334] For reference purposes, specific numbers (= example number) were assigned to individual compounds in Tables 2 to 24f below, where the example number in question consists of the number of the chemical formula assigned to the respective table and a “number line ”(line number) which refers to the same number in the row in the first column of Table 1. The chemical structure of example no. “(Formula number) (line number)” is thus unambiguously defined by the previous formula in the respective table by the formula number and line number in table 1, for example:

example no. “Iaa1” in Table 2 is the compound of structural formula (Ia), where A ¹ = O [= formula (Iaa)] and Q = OH, (R ¹ ) m = 3-F and (R ² ) n = 4-Cl, defined according to line 1 of table 1, or a tautomer thereof;

example no. “Iad204” in Table 2 is the compound of structural formula (Ia), where A ¹ = N-OH [= formula (Iad)] and Q = OH, (R ¹ ) m = 3,4-Cl2 and (R ² ) n = 4-F, defined according to line 204 of table 1, or a tautomer thereof.

[335] Correspondingly, this applies to the allocation of

169/289 stereoisomers threus or racemic or optically active erythro stereoisomers. For example, for reference purposes, specific numbers (= example number) were assigned to the compounds in Table 2a, where the number "treo-laa (line number)" designates the racemic mixture of the treo enantiomers that have the chemical structure of structural formulas (treo-1-laa) and (treo-2laa), each of which has the structural combination of groups Q, (R ¹ ) m and (R ² ) n according to the line number in table 1.

[336] Table 2: compounds of structural formulas (Ia), (laa), (lab), (lac), (lad), (lae), (laf), (lag) and (lah), where each groups Q, (R ¹ ) m and (R ² ) n have the meaning defined in table 1:

(Ia) (laa) A ¹ is (= 0) (lab) A ¹ is (= S) (lac) A ¹ is (= N-CH ₃ ) (lad) A ¹ is (= N-OH) (lae ) A ¹ is (= N-OCH ₃ ) (laf) A ¹ is (= N-NH ₂ ) (lag) A ¹ is [= NN (CH ₃ ) J (lah) A ¹ is (= N-benzyl) [337] Table 2, examples of erythro / threo mixtures (proportions from 70:30 to 30:70):

[338] Examples of compounds of structural formulas (laa) to (lah) refer to the compounds of the respective structural formulas (laa) to (lah), in each case in the form of an erythro / racemic mixture (proportions of 70: 30 to 30:70), where the meaning of the groups Q, (R ¹ ) m and (R ² ) n is defined according to a line number in Table 1. The individual compounds are numbered “(formula) (number of line) ”, without any parentheses, for example, laa50 = compound of structural formula (laa), where Q = OSO2 (4-Me-Ph), (R ¹ ) m = 3,420 difluoro and (R ² ) n = 3 fluorine, according to line 50 of table 1.

[339] Tables 2a to 2f: compounds of structural formulas (treo-laa) and (treo-2laa), in which each of the groups Q, (R ¹ ) m and (R ² ) does not have the defined meaning

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(treo-laa) = (treo-1-laa) + (treo-2-laa) (50:50) = (rac.) [340] Table 2a (treo racemates), examples:

[341] Compounds of structural formula (laa) in the form of a racemic mixture 5 of the isomers treo [= formula (treo-laa)], where the structural combination of groups Q, (R ¹ ) m (R ² ) n is not defined according to a line number in Table 1.

[342] The numbering is “treo-laa (line number)”.

[343] Table 2b (optically active treo-2 compounds), examples:

[344] Optically active treo-2 enantiomers in an enriched form [= form (2R, 3R) greater than 90% ee] which have the chemical structure of the structural formula (treo-2-laa), in which the structural combination of the groups Q, (R ¹ ) m (R ² ) _n is defined according to a line number in Table 1.

[345] The numbering is “treo-2-laa (line number)”.

[346] Table 2c (optically active treo-1 enantiomers), examples:

[347] Treo-1 optically active enantiomers in an enriched form [= form (2S, 3S) greater than 90% ee] which have the chemical structure of the structural formula (treo-1-laa), in which the structural combination of the groups Q, (R ¹ ) m (R ² ) n is defined according to a line number in Table 1.

[348] In this case, an individual enantiomer is assigned the number “treo-1laa (line number)”. For example, No. treo-1-laa5 refers to the compound of structural formula (treo-1-laa), where Q = OH, (R ¹ ) m = 3-F and (R ² ) n = 4-Br.

171/289 [349] Table 2d (erythro racemates), examples:

[350] Compounds of structural formula (Iaa) in the form of a racemic mixture of erythro isomers [= formula (erythro-Iaa)], where the structural combination of the groups Q, (R ¹ ) m and (R ² ) n is not defined according to a line number in Table 1.

[351] The numbering is “erythro-Iaa (line number)”.

[352] Table 2e (erythro-1 enantiomers), examples:

[353] Optically active erythro-1 enantiomers in an enriched form [= form (2R, 3S) greater than 90% ee] which have the chemical structure of the structural formula (Iaa) in the form of erythro-1 [= formula (erythro- 1-Iaa)], where the structural combination of the groups Q, (R ¹ ) m and (R ² ) n is defined according to a row number in Table 1.

[354] The numbering is “erythro-1-Iaa (line number)”.

[355] Table 2f (erythro-2 enantiomers) examples:

[356] Optically active erythro-2 enantiomers in an enriched form [= form (2S, 3R) greater than 90% ee] which have the chemical structure of the structural formula (Iaa) in the form erythro-2 [= formula (erythro-2 -Iaa)], where the structural combination of groups Q, (R ¹ ) m and (R ² ) n is defined according to a line number in Table 1.

[357] The numbering is “erythro-2-Iaa (line number)”.

[358] Table 3: compounds of structural formulas (Ib), (Iba), (Ibb), (Ibc), (Ibd), (Ibe), (Ibf), (Ibg) and (Ibh), where each groups Q, (R ¹ ) m and (R ² ) n have the

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(Ib) (lba) A ¹ is (= 0) (lbb) A ¹ is (= S) (lbc) A ¹ is (= N-CH ₃ ) (lbd) A ¹ is (= N-0H) (lbe ) A ¹ is ^ N-OCHJ (lbf) A ¹ is (= N-NH ₂ ) (lbg) A ¹ is [= NN (CH ₃ ) ₂ ] (lbh) A ¹ is (= N-benzyl) [359 ] Table 3, examples of erythro / threo mixtures (proportions from 70:30 to 30:70):

[360] Examples include the compounds of the respective structural formulas (laa) to (lah), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in which the meanings of groups Q, (R ¹ ) m (R ² ) n are defined according to a line number in Table 1. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[361] Table 4: compounds of structural formulas (Ic), (Ica), (Icb), (Icc), (Icd), (Ice), (Icf), (Icg) and (Ich), where each groups Q, (R ¹ ) m and (R ² ) n have the meaning defined in table 1:

(Ic) (lca) A ¹ o (= 0) (lcb) A ¹ is (= S) (lcc) A ¹ o (= N-CH ₃ ) (lcd) A ¹ is (= N-OH) (lce ) A ¹ is (= N-OCH ₃ ) (lcf) A ¹ ó (= N-NH ₂ ) (lcg) A ¹ Ó [= NN (CH ₃ ) ₂ ] (lch) A ¹ is (= N-benzyl ) [362] Table 4, examples of erythro / threo mixtures (proportions from 70:30 to 30:70):

173/289 [363] Examples are the compounds of the respective structural formulas (Ica) to (Ich), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), where the meanings of the groups Q, (R ¹ ) m (R ² ) n are defined according to a line number in Table 1. The individual compounds are numbered “(formula) (line number)”, without any parentheses .

[364] Table 5: compounds of structural formulas (Id), (Ida), (Idb), (Ide), (Idd), (Ide), (Idf), (Idg) and (Idh), where each groups Q, (R ¹ ) m and (R ² ) n have the meaning defined in table 1:

(Id) (lda) A ¹ is (= O) (ldb) A ¹ is (= S) (Ide) A ¹ is (= N-CH ₃ ) (ldd) A ¹ ó (= N-OH) (lde ) A ¹ is (= N-OCH ₃ ) (ldf) A ^{1 is} (= N-NH ₂ ) (ldg) A ¹ is [= NN (CH ₃ ) 2] (ldh) A ^{1 is} (= N-benzll ) [365] Table 5, examples of erythro / threo mixtures (proportions from 70:30 to 30:70):

[366] Examples include the compounds of the respective structural formulas (Ida) to (Idh), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in which the meanings of groups Q, (R ¹ ) m (R ² ) n are defined according to a line number in Table 1. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[367] Table 6: compounds of structural formulas (le), (lea), (leb), (lec), (led), (lee), (lef), (leg) and (leh), in which each groups Q, (R ¹ ) m and (R ² ) n have the meaning defined in table 1:

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(le) (lea) A ¹ is (= O) (leb) A ¹ O (= Y) (lec) A ¹ is (= N-CH3) (led) A ¹ is (= N-OH) (lee) A ¹ O (= N-OCH ₃ ) (lef) A ¹ O (= N-NH ₂ ) (leg) A ¹ O [= NN (CH ₃ ) ₂ ] (leh) A ¹ is (= N-benzyl)

[368] Table 6, examples of erythro / threo mixtures (proportions from 70:30 to 30:70):

[369] Examples include the compounds of the respective structural formulas (lea) to (leh), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in which the meanings of groups Q, (R ¹ ) m (R ² ) _n are defined according to a line number in Table 1. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[370] Tables 6a to 6f: compounds of structural formulas (treo-lea) and (treo-2lea), in which each of the groups Q, (R ¹ ) m and (R ² ) does not have the meaning defined in table 1:

(treo-lea) = (treo-1-lea) + (treo-2-lea) (50:50) = (rac.) [371] Table 6a (racemates), examples:

175/289 [372] Structural formula (lea) compounds in the form of racemic mixture of the treo [= formula (treo-Iea)], in which the structural combination of the groups Q, (R ¹ ) me (R ² ) n is defined according to a line number in Table 1.

[373] The individual compounds are numbered “treo-Iea (line number)”.

[374] Table 6b (optically active treo-2 enantiomers), examples:

[375] Optically active treo-2 enantiomers in an enriched form [= form (2R, 3R) greater than 90% ee] which have the chemical structure of the structural formula (treo-2-Iea), in which the structural combination of the groups Q, (R ¹ ) m and (R ² ) n are defined according to a line number in Table 1. The individual compounds are numbered “treo-2-Iea (line number)”.

[376] Table 6c (optically active treo-1 enantiomers), examples:

[377] Optically active treo-1 enantiomers in an enriched form [= form (2S, 3S) greater than 90% ee] which have the chemical structure of the structural formula (treo-1-Iea), in which the structural combination of the groups Q, (R ¹ ) m and (R ² ) n are defined according to a line number in Table 1. The individual compounds are numbered “treo-1-Iea (line number)”.

[378] Table 6d (erythro racemates), examples:

[379] Compounds of structural formula (Iea) in the form of a racemic mixture of erythro isomers [= formula (erythro-Iea)], where the structural combination of groups Q, (R ¹ ) m (R ² ) n is not defined according to a line number in Table 1. The individual compounds are numbered “erythro-Iea (line number)”.

[380] Table 6e (erythro-1 enantiomers), examples:

[381] Optically active erythro-1 enantiomers in an enriched form [= form (2R, 3S) greater than 90% ee] which have the chemical structure of the structural formula (Iea) in the form erythro-1 [= formula (erythro-1 -Iea)], where the structural combination of the groups Q, (R ¹ ) m and (R ² ) n is defined according to a line number in Table 1. The individual compounds are numbered “erythro1-Iea (line number ) ”.

176/289 [382] Table 6f (erythro-2 enantiomers) examples:

[383] Optically active erythro-2 enantiomers in an enriched form [= form (2S, 3R) greater than 90% ee] which have the chemical structure of the structural formula (lea) in the form erythro-2 [= formula (erythro-2 -lea)], where the structural combination of the groups Q, (R ¹ ) m and (R ² ) n is defined according to a line number in Table 1. The individual compounds are numbered “eritro2-lea (line number ) ”.

[384] Table 7: compounds of structural formulas (If), (Ifa), (Ifb), (Ifc), (Ifd), (Ife), (Iff), (Ifg) and (Ifh), where each groups Q, (R ¹ ) m and (R ² ) n have the meaning defined in table 1:

(If) (Ifa) A ¹ is (= O) (Ifb) A ¹ is (= Y) (Ifc) A ¹ is (= N-CH3) (Ifd) A ¹ is (= N-OH) (Ife) A ¹ is (= N-OCH3) (Iff) A ¹ is (= N-NH2) (Ifg) Ai is [sN-NfCH ^ (Ifh) A ¹ is (= N-benzyl)

[385] Table 7, examples of erythro / threo mixtures (proportions from 70:30 to 30:70):

[386] Examples are the compounds of the respective structural formulas (Ifa) to (Ifh), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in which the meanings of groups Q, (R ¹ ) m (R ² ) n are defined according to a line number in Table 1. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[387] Tables 7a to 7f: compounds of structural formulas (treo-lfa) and (treo-220 Ifa), in which each of the groups Q, (R ¹ ) me (R ² ) does not have the meaning defined in table 1 :

177/289

(treo-lfa) = (treo-1-lfa) + (treo-2-lfa) (50:50) = (rac.) [388] Table 7a (treo racemates), examples:

[389] Compounds of structural formula (Ifa) in the form of racemic mixture of the isomers treo [= formula (treo-lfa)], in which the structural combination of the groups Q, (R ¹ ) m (R ² ) n is defined according to a line number in Table 1. The individual compounds are numbered “treo-2-alpha (line number)”.

[390] Table 7b (optically active treo-2 compounds), examples:

[391] Optically active treo-2 enantiomers in an enriched form [= form (2R, 3R) greater than 90% ee] which have the chemical structure of the structural formula (treo-2-lfa), in which the structural combination of the groups Q, (R ¹ ) m and (R ² ) _n are defined according to a line number in Table 1. The individual compounds are numbered "treo-2-lfa (line number)".

[392] Table 7c (optically active treo-1 enantiomers), examples:

[393] Optically active treo-1 enantiomers in an enriched form [= form (2S, 3S) greater than 90% ee] which have the chemical structure of the structural formula (treo-1-Ifa), in which the structural combination of the groups Q, (R ¹ ) m and (R ² ) _n are defined according to a line number in Table 1. The individual compounds are numbered "treo-1-alpha (line number)".

[394] Table 7d (erythro racemates), examples:

[395] Compounds of structural formula (Ifa) in the form of a racemic mixture of erythro isomers [= formula (erythro-lfa)], where the combination

178/289 structural group Q, (R ¹ ) m and (R ² ) n is defined according to a line number in Table 1. The individual compounds are numbered "erythro-lfa (line number)".

[396] Table 7e (erythro-1 enantiomers), examples:

[397] Optically active erythro-1 enantiomers in an enriched form [= form (2R, 3S) greater than 90% ee] which have the chemical structure of the structural formula (Ifa) in erythro-1 form [= formula (erythro-1 -Ifa)], where the structural combination of the groups Q, (R ¹ ) m and (R ² ) n is defined according to a row number in Table 1. The individual compounds are numbered “eritro10 1-alpha (number of line)".

[398] Table 7f (erythro-2 enantiomers) examples:

[399] Optically active erythro-2 enantiomers in an enriched form [= form (2S, 3R) greater than 90% ee] which have the chemical structure of the structural formula (Ifa) in form erythro-2 [= formula (erythro-2 -lfa)], where the structural combination of groups Q, (R ¹ ) m and (R ² ) _n is defined according to a line number in Table 1. The individual compounds are numbered “erythro2-lfa (line number ) ”.

[400] Table 8: compounds of structural formulas (Ig), (Iga), (Igb), (Igc), (Igd), (Ige), (Igf), (Igg) and (Igh), where each groups Q, (R ¹ ) m and (R ² ) n have the meaning defined in table 1:

O

(IG)

Iga) A ¹ is = O) (lgb) A ¹ is (= S) (lgc) A ¹ is (= N-CH ₃ ) (lgd) A ¹ is (= N-OH) (lge) A ¹ is ( = N-OCH ₃ ) (lgf) A ¹ is (= N-NH ₂ ) (lgg) A ¹ is FN-NÍCHjh] (lgh) A ¹ is (= N-benzll) [401] Table 8, examples of mixtures eritro / treo (proportions from 70:30 to 30:70):

179/289 [402] Examples include the compounds of the respective structural formulas (Iga) to (Igh), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), where the meanings of the groups Q, (R ¹ ) m (R ² ) n are defined according to a line number in Table 1. The individual compounds are numbered “(formula) (line number)”, without any parentheses .

[403] Table 9: compounds of structural formulas (Ih), (lha), (Ihb), (him), (Ihd), (him), (Ihf), (Ihg) and (Ihh), where each groups Q, (R ¹ ) m and (R ² ) n have the meaning defined in table 1:

(R ² l

(Ih) lha) A ¹ is (= O) (Ihb) A ¹ is (= Y) (him) A ¹ is (= n-ch ₃ ) (Ihd) A ¹ is (= NOH) (him) A ¹ is (= N-OCH ₃ ) (Ihf) A ¹ is (= N-NH ₂ ) (Ihg) A ¹ is [= NN (CH ₃ ) ₂ ] (Ihh) A ¹ is (= N-benzyl)

[404] Table 9, examples of erythro / threo mixtures (proportions from 70:30 to 30:70):

[405] Examples include the compounds of the respective structural formulas (lha) to (Ihh), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in which the meanings of groups Q, (R ¹ ) m (R ² ) n are defined according to a line number in Table 1. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[406] Tables 9a to 9f: compounds of structural formulas (treo-lha) and (treo-2Iha), in which each of the groups Q, (R ¹ ) m and (R ² ) does not have the meaning defined in table 1:

180/289

(treo-lha) = (treo-1-iha) + (treo-2-lha) (50:50) = (rac.) [407] Table 9a (treo racemates), examples:

[408] Structural formula (lha) compounds in the form of a racemic mixture of the treo [= formula (treo-lha)], in which the structural combination of the groups Q, (R ¹ ) m and (R ² ) n is defined according to a line number in Table 1. The individual compounds are numbered “treo-2-lha (line number)”.

[409] Table 9b (optically active treo-2 compounds), examples:

[410] Treo-2 optically active enantiomers in an enriched form [= form (2R, 3R) greater than 90% ee] which have the chemical structure of the structural formula (treo-2-lha), in which the structural combination of the groups Q, (R ¹ ) m and (R ² ) _n are defined according to a line number in Table 1. The individual compounds are numbered “treo-2-lha (line number)”.

[411] Table 9c (optically active treo-1 enantiomers), examples:

[412] Optically active treo-1 enantiomers in an enriched form [= form (2S, 3S) greater than 90% ee] which have the chemical structure of the structural formula (treo-1-lha), in which the structural combination of the groups Q, (R ¹ ) m and (R ² ) _n are defined according to a line number in Table 1. The individual compounds are numbered "treo-1-line (line number)".

[413] Table 9d (erythro racemates), examples:

[414] Compounds of structural formula (lha) in the form of a racemic mixture of erythro isomers [= formula (erythro-lfa)], where the combination

181/289 structural group Q, (R ¹ ) m and (R ² ) n is defined according to a line number in Table 1. The individual compounds are numbered “erythro-line (line number)”.

[415] Table 9e (erythro-1 enantiomers), examples:

[416] Optically active erythro-1 enantiomers in an enriched form [= form (2R, 3S) greater than 90% ee] which have the chemical structure of the structural formula (lha) in the form erythro-1 [= formula (erythro-1 line), where the structural combination of groups Q, (R ¹ ) m and (R ² ) n is defined according to a row number in Table 1. The individual compounds are numbered “erythro10 1-line (number of line)".

[417] Table 9f (erythro-2 enantiomers) examples:

[418] Optically active erythro-2 enantiomers in an enriched form [= form (2S, 3R) greater than 90% ee] which have the chemical structure of the structural formula (lha) in the form erythro-2 [= formula (erythro-2 line), where the structural combination of groups Q, (R ¹ ) m and (R ² ) _n is defined according to a line number in Table 1. The individual compounds are numbered “erythro2-line (line number ) ”.

[419] Table 10: compounds of structural formulas (li), (lia), (lib), (lic), (lid), (lie), (lif), (lig) and (lih), where each groups Q, (R ¹ ) m and (R ² ) n have the meaning defined in table 1:

n (li) lia) A ¹ _is (= θ) (lib) A ¹ _is (= S) (lic) A ¹ is (= N-CH ₃ ) (lid) A ¹ _is (= N-OH) (lie ) Ai is (= N-OCH ₃ ) (lif) A ¹ is (= N-NH ₂ ) (lig) A ¹ _is [= NN (CH ₃ b] (lih) A ¹ is (= N-benzyl) [ 420] Table 10, examples of erythro / threo mixtures (proportions from 70:30 to

182/289

30:70):

[421] Examples include the compounds of the respective structural formulas (lia) to (lih), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in which the meanings of groups Q, (R ¹ ) m (R ² ) n are defined according to a line number in Table 1. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[422] Table 11: compounds of structural formulas (Ik), (Ika), (Ikb), (Ikc), (Ikd), (Ike), (Ikf), (Ikg) and (Ikh), where each groups Q, (R ¹ ) m and (R ² ) n have the meaning defined in table 1:

(Ik) (Ika) A ¹ is (= O) (Ikb) A ¹ is (= Y) (Ikc) A ¹ is (= N-CH3) (Ikd) A ¹ is (= N-OH) (Ike) A ¹ is (= N-OCH ₃ ) (Ikf) A ¹ is (= N-NH ₂ ) (Ikg) A ¹ is [= NN (CH ₃ ) 2] (Ikh) A ¹ is (= N-benzyl)

[423] Table 11, examples of erythro / threo mixtures (proportions from 70:30 to

30:70): Examples include the compounds of the respective structural formulas (Ika) to (Ikh), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in that the meanings of the groups Q, (R ¹ ) m (R ² ) n are defined according to a line number in Table 1. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[424] Table 12: compounds of structural formulas (IL), (ILa), (ILb), (ILc), (ILd), (ILe), (ILf), (ILg) and (ILh), where each groups Q, (R ¹ ) m and (R ² ) n have the meaning defined in table 1:

183/289

(IL) (ILa) A ¹ is (= O) (ILb) A ¹ is (= S) (ILc) A ¹ is (= N-CH3) (ILd) A ¹ is (= N-OH) (ILe) A ¹ is (= N-OCHj) (ILf) A ¹ is (= N-NH2) (ILg) A ¹ is [= NN (CH3) ₂ ] (ILh) A ¹ is (= N-benzyl) [425] Table 12, examples of erythro / threo mixtures (proportions from 70:30 to

30:70): Examples include the compounds of the respective structural formulas (ILa) to (ILh), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in that the meanings of the groups Q, (R ¹ ) m (R ² ) n are defined according to a line number in Table 1. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[426] Table 13: compounds of structural formulas (Im), (Ima), (Imb), (Imc), (Imd), (Ime), (Imf), (Img) and (Imh), where each groups Q, (R ¹ ) m and (R ² ) n have the meaning defined in table 1:

(Im) (Magnet) A ¹ is (= O) (Imb) A ¹ is (= S) (Imc) THE' is (= N-CH ₃ ) (Imd) A ¹ is (= N-OH) (Ime) A ¹ is (= N-OCH ₃ ) (Imf) A ¹ is (= N-NH ₂ ) (Img) A ¹ is UN-NÍCHj),] (Imh) A ¹ is (= N-benzyl)

[427] Table 13, examples of erythro / threo mixtures (proportions from 70:30 to

184/289

30:70): Examples include the compounds of the respective structural formulas (Ima) to (Imh), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in that the meanings of the groups Q, (R ¹ ) m (R ² ) n are defined according to a line number in Table 1. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[428] Table 14: compounds of structural formulas (In), (Ina), (Inb), (Inc), (Ind), (Ine), (Inf), (Ing) and (Inh), where each groups Q, (R ¹ ) m and (R ² ) n have the meaning defined in table 1:

(In) (lna) A ¹ is (= O) (lnb) A ¹ is (= S) (lnc) A ¹ is (= N-CH3) (lnd) A ¹ is (= N-OH) (lne) A ¹ is (= N-OCHj) (lnf) A ¹ is (= N-NH ₂ ) (lng) A ¹ is [= NN (CH ₃ ) ₂ ] (lnh) A ¹ is (= N-benzyl) [ 429] Table 14, examples of erythro / threo mixtures (proportions from 70:30 to

30:70): Examples include the compounds of the respective structural formulas (Ina) to (Inh), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in that the meanings of the groups Q, (R ¹ ) m and (R ² ) n are defined according to a line number in Table 1. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[430] Table 15: compounds of structural formulas (Io), (loa), (lob), (loc), (lod), (loe), (lof), (log) and (loh), where each groups Q, (R ¹ ) m and (R ² ) n have the meaning defined in table 1:

185/289

(Io) (loa) A ¹ is (= O) (lob) A ¹ is (= Y) (loc) A ¹ is (= N-CH ₃ ) (lod) A ¹ is (= N-OH) (loe) A ¹ is (= N-OCH ₃ ) (lof) A ¹ is (= N-NH ₂ ) (log) A ¹ is [= NN (CH ₃ ) ₂ ] (loh) A ¹ is (= N-benzyl)

[431] Table 15, examples of erythro / threo mixtures (proportions from 70:30 to

30:70): Examples include the compounds of the respective structural formulas (loa) to (loh), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in that the meanings of the groups Q, (R ¹ ) m (R ² ) n are defined according to a line number in Table 1. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[432] Table 16: compounds of structural formulas (Ip), (Ipa), (Ipb), (Ipc), (Ipd), (Ipe), (Ipf), (Ipg) and (Iph), where each groups Q, (R ¹ ) m and (R ² ) n have the meaning defined in table 1:

(Ip) (lpa) A ¹ is (= O) (lpb) A ¹ is (= S) (lpc) A ¹ is (= N-CH ₃ ) (lpd) A ¹ is (= N-OH) (lpe ) A ¹ is (= N-OCH.j) (lpf) A ¹ is (= N-NH ₂ ) (lpg) A ¹ is [= NN (CH ₃ ) 2] (lph) A ¹ is (= N- benzyl) [433] Table 16, examples of erythro / threus mixtures (proportions from 70:30 to

186/289

30:70):

[434] Examples include the compounds of the respective structural formulas (Ipa) to (Iph), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in which the meanings of groups G, (R ¹ ) m (R ² ) n are defined according to a line number in Table 1. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[435] Framework 17: compounds of structural formulas (Iq), (Iqa), (Iqb), (Iqc), (Iqd), (Iqe), (Iqf), (Iqg) and (Iqh), where each of groups G, (R ¹ ) m (R ² ) n has the meaning defined in table 1:

(I Q) (Iqa) A ¹ is (= O) (Iqb) A ¹ is (= Y) (Iqc) A ¹ is (= N-CH ₃ ) (Iqd) A ¹ is (= N-OH) (Iqe) A ¹ is UN-OCH-j) (Iqf) A ¹ is (= N-NH ₂ ) (Iqg) A1 is [= NN (CH ₃ ) ₂ ] (Iqh) A ¹ is (= N-benzyl)

[436] Guadro 17, examples of erythro / threo mixtures (proportions from 70:30 to 30:70):

[437] Examples include the compounds of the respective structural formulas (Iqa) to (Iqh), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), where the meanings of the groups Q, (R ¹ ) m (R ² ) n are defined according to a line number in Table 1. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[438] Table 18: compounds of structural formulas (Ir), (Ira), (Irb), (Ire), (Ird), (Ire), (Irf), (Irg) and (Irh), where each groups Q, (R ¹ ) m and (R ² ) n have the

187/289 meaning defined in Table 1:

(Go) (Will) A ¹ is (= O) (Irb) A ¹ is (= Y) (Ire) A ¹ is (= N-CH ₃ ) (Ird) A ¹ is (= N-OH) (Ire) A ¹ is (= N-OCH ₃ ) (Irf) A ¹ is (= N-NH ₂ ) (irg) A ¹ is [= N-N (CH3) 2] (Irh) A ¹ is (= N-benzyl)

[439] Table 18, examples of erythro / threo mixtures (proportions from 70:30 to 30:70):

[440] Examples include the compounds of the respective structural formulas (Ira) to (Irh), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in which the meanings of groups Q, (R ¹ ) m (R ² ) n are defined according to a line number in Table 1. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[441] Table 19: compounds of structural formulas (Is), (Isa), (Isb), (Isc), (Isd), (Ise), (Isf), (Isg) and (Ish), where each groups Q, (R ¹ ) m and (R ² ) n have the

188/289

(Is) (lsa) A ¹ is (= O) (lsb) A ¹ is (= S) (lsc) A ¹ is (= N-CH ₃ ) (lsd) A ¹ is (= N-OH) (lse ) A ¹ is (= N-OCH ₃ ) (lsf) A ¹ is (= N-NH ₂ ) (lsg) Ai is [= NN (CH3) ₂ ] (lsh) A ¹ is (= N-benzyl) [ 442] Table 19, examples of erythro / threo mixtures (proportions from 70:30 to 30:70):

[443] Examples include the compounds of the respective structural formulas (Isa) to (Ish), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), where the meanings of the groups Q, (R ¹ ) m (R ² ) n are defined according to a line number in Table 1. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[444] Table 20: compounds of structural formulas (It), (Ita), (Itb), (Itc), (Itd), (Ite), (Itf), (Itg) and (Ith), where each groups Q, (R ¹ ) m and (R ² ) n have the

189/289

(lt) (lta) A ¹ is (= 0) (ltb) A ¹ is (= S) (ltc) A ¹ is (= N-CH ₃ ) (ltd) A ¹ is (= N-0H) (lte ) A ¹ is (= N-0CH ₃ ) (ltf) A ¹ is (= N-NH ₂ ) (ltg) A ¹ is [= NN (CH ₃ ) ₂ ] (lth) A ¹ is (= N-benzll ) [445] Table 20, examples of erythro / threo mixtures (proportions from 70:30 to 30:70):

[446] Examples include the compounds of the respective structural formulas 5 (Ita) to (Ith), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in which the meanings of the groups Q, (R ¹ ) m (R ² ) n are defined according to a line number in Table 1. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[447] Tables 20a to 20f: composed of structural formulas (treo-lta) and (treo-2 Ita), in which each of the groups Q, (R ¹ ) me (R ² ) n does not have the defined meaning

190/289

(R), (treo-1 -Ita) (treo-2-lta) (treo-lta) = (treo-1-lta) + (treo-2-lta) (50:50) = (rac.) [ 448] Table 20a (trematous racemates), examples:

[449] Structural formula (Ita) compounds in the form of racemic mixture of the treo [= formula (treo-lta)], in which the structural combination of the groups Q, (R ¹ ) m (R ² ) n is defined according to a line number in Table 1. The individual compounds are numbered “treo-lta (line number)”.

[450] Table 20b (optically active treo-2 compounds), examples:

[451] Optically active treo-2 enantiomers in an enriched form [= form (2R, 3R) greater than 90% ee] which have the chemical structure of the structural formula (treo-2-lta), in which the structural combination of the groups Q, (R ¹ ) m and (R ² ) _n are defined according to a line number in Table 1. The individual compounds are numbered “treo-2-lta (line number)”.

[452] Table 20c (optically active treo-1 enantiomers), examples:

[453] Optically active treo-1 enantiomers in an enriched form [= form (2S, 3S) greater than 90% ee] which have the chemical structure of the structural formula (treo-1-Ita), in which the structural combination of the groups Q, (R ¹ ) m and (R ² ) _n are defined according to a line number in Table 1. The individual compounds are numbered “treo-1 -lta (line number)”.

[454] Table 20d (racemates erythro), examples:

[455] Compounds of structural formula (Ita) in the form of a racemic mixture of erythro isomers [= formula (erythro-lta)], in which the combination

191/289 structural group Q, (R ¹ ) m and (R ² ) n is defined according to a line number in Table 1. The individual compounds are numbered “erythro-lta (line number)”.

[456] Table 20e (erythro-1 enantiomers), examples:

[457] Optically active erythro-1 enantiomers in an enriched form [= form (2R, 3S) greater than 90% ee] which have the chemical structure of the structural formula (Ita) in the form erythro-1 [= formula (erythro-1 -Ita)], where the structural combination of the groups Q, (R ¹ ) m and (R ² ) n is defined according to a line number in Table 1. The individual compounds are numbered “eritro10 1 -lta (number of line)".

[458] Table 20f (erythro-2 enantiomers) examples:

[459] Optically active erythro-2 enantiomers in an enriched form [= form (2S, 3R) greater than 90% ee] which have the chemical structure of the structural formula (Ita) in the form erythro-2 [= formula (erythro-2 -lta)], where the structural combination of the groups Q, (R ¹ ) m and (R ² ) _n is defined according to a line number in Table 1. The individual compounds are numbered “erythro2-lta (line number ) ”(Similar to Table 20b).

[460] Table 21: compounds of structural formulas (lu), (moon), (lub), (luc), (lud), (lue), (luf), (lug) and (luh), where each groups Q, (R ¹ ) m and (R ² ) n have the meaning defined in table 1:

N — N ^ 2 * ^ 5

(lu) (moon) A ¹ is (= O) (lub) A ¹ is (= S) (luc) A ¹ is (= N-CH ₃ ) (lud) A ¹ is (= N-OH) (lue ) A ¹ is (= N-OCH3) (luf) A ¹ is (= N-NH ₂ ) (lug) A ¹ is UN-NÍCH ^ J (luh) A ¹ is (= N-benzyl)

192/289 [461] Table 21, examples of erythro / threo mixtures (proportions from 70:30 to

30:70): Examples include the compounds of the respective structural formulas (moon) to (luh), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in that the meanings of the groups Q, (R ¹ ) m (R ² ) n are defined according to a line number in Table 1. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[462] Tables 21a to 21 f: composed of structural formulas (treo-moon) and (treo2-moon), in which each of the groups Q, (R ¹ ) m and (R ² ) n has the meaning defined in table 1 :

(treo-lua) = (treo-1-lua) + (treo-2-lua) (50:50) = (rac.) [463] Table 21a (treo racemates), examples:

[464] Structural formula (moon) compounds in the form of a racemic mixture of the treo [= formula (treo-moon)] isomers, in which the structural combination of the groups Q, (R ¹ ) m and (R ² ) n is defined according to a line number in Table 1. The individual compounds are numbered “treo-moon (line number)”.

[465] Table 21b (optically active treo-2 compounds), examples:

[466] Optically active treo-2 enantiomers in an enriched form [= form (2R, 3R) greater than 90% ee] which have the chemical structure of the structural formula (treo-2-moon), in which the structural combination of the groups Q, (R ¹ ) m and (R ² ) _n are defined according to a line number in Table 1. The compounds

193/289 individual numbers are numbered “treo-2-Iua (line number)”.

[467] Table 21c (optically active treo-1 enantiomers), examples:

[468] Optically active treo-1 enantiomers in an enriched form [= form (2S, 3S) greater than 90% ee] which have the chemical structure of the structural formula (treo-1-Iua), in which the structural combination of the groups Q, (R ¹ ) m (R ² ) n is defined according to a line number in Table 1. The individual compounds are numbered “treo-1-Iua (line number)”.

[469] Table 21d (erythro racemates), examples:

[470] Compounds of structural formula (Iua) in the form of a racemic mixture of erythro isomers [= formula (erythro-Iua)], in which the structural combination of groups Q, (R ¹ ) m (R ² ) n is defined according to a line number in Table 1. The individual compounds are numbered “erythro-Iua (line number)”.

[471] Table 21e (erythro-1 enantiomers), examples:

[472] Optically active erythro-1 enantiomers in an enriched form [= form (2R, 3S) greater than 90% ee] which have the chemical structure of the structural formula (Iua) in the form erythro-1 [= formula (erythro-1 -Iua)], where the structural combination of groups Q, (R ¹ ) m and (R ² ) n is defined according to a line number in Table 1. The individual compounds are numbered “erythro1- Iua (line number ) ”.

[473] Table 21f (erythro-2 enantiomers) examples:

[474] Optically active erythro-2 enantiomers in an enriched form [= form (2S, 3R) greater than 90% ee] which have the chemical structure of the structural formula (Iua) in the form erythro-2 [= formula (erythro-2 -Iua)], where the structural combination of the groups Q, (R ¹ ) m and (R ² ) n is defined according to a line number in Table 1. The individual compounds are numbered “erythro2- Iua (line number ) ”.

[475] Table 22: compounds of structural formulas (Iv), (Ivva), (Ivb), (Ivc), (Ivd), (Ivve), (Ivf), (Ivg) and (Ivh), where each groups Q, (R ¹ ) m and (R ² ) n have the meaning defined in table 1:

194/289

Ν — Ν ✓

CH '3

TI (Ιν) (lva) A ¹ is (= Ο) (lvb) A ¹ is (= S) (lvc) A ¹ is (= N-CH ₃ ) (lvd) A ¹ is (= N-OH) ( lve) A ¹ is (= N-OCH ₃ ) _(R 2) (Ivf) A ¹ is (= N-NH ₂ ) (lvg) A ¹ is FN-NÍCH,),] (lvh) A ¹ is (= N-benzyl) [476] Table 22, examples of erythro / threus mixtures (proportions from 70:30 to 30:70):

[477] Examples include the compounds of the respective structural formulas (Iva) to (Ivh), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in which the meanings of groups Q, (R ¹ ) m (R ² ) n are defined according to a line number in Table 1. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[478] Tables 22a to 22f: compounds of structural formulas (treo-lva) and (treo2-lva), in which each of the groups Q, (R ¹ ) m and (R ² ) does not have the meaning defined in table 1:

CH, / 4

CH, / 3

N-N

(treo-1-lva) (treo-2-lva) (treo-lva) = (treo-1-lva) + (treo-2-lva) (50:50) = (rac.)

195/289 [479] Table 22a (trematite racemates), examples:

[480] Structural formula (Iva) compounds in the form of racemic mixture of the treo [= formula (treo-Iva)], in which the structural combination of the groups Q, (R ¹ ) m and (R ² ) n is defined according to a line number in Table 1. The individual compounds are numbered “treo-Iva (line number)”.

[481] Table 22b (optically active treo-2 compounds), examples:

[482] Optically active treo-2 enantiomers in an enriched form [= form (2R, 3R) greater than 90% ee] which have the chemical structure of the structural formula (treo-2-Iva), in which the structural combination of the groups Q, (R ¹ ) m and (R ² ) n are defined according to a line number in Table 1. The individual compounds are numbered “treo-2-Iva (line number)”.

[483] Table 22c (optically active treo-1 enantiomers), examples:

[484] Optically active treo-1 enantiomers in an enriched form [= form (2S, 3S) greater than 90% ee] which have the chemical structure of the structural formula (treo-1-Iva), in which the structural combination of the groups Q, (R ¹ ) m and (R ² ) n are defined according to a line number in Table 1. The individual compounds are numbered “treo-1-Iva (line number)”.

[485] Table 22d (erythro racemates), examples:

[486] Compounds of structural formula (Iva) in the form of a racemic mixture of erythro isomers [= formula (erythro-Iva)], where the structural combination of groups Q, (R ¹ ) m (R ² ) n is not defined according to a line number in Table 1. The individual compounds are numbered “erythro-Iva (line number)”.

[487] Table 22e (erythro-1 enantiomers), examples:

[488] Optically active erythro-1 enantiomers in an enriched form [= form (2R, 3S) greater than 90% ee] which have the chemical structure of the structural formula (Iva) in the form erythro-1 [= formula (erythro-1 -Iva)], where the structural combination of groups Q, (R ¹ ) m and (R ² ) n is defined according to a line number in Table 1. The individual compounds are numbered “erythro1-Iva (line number ) ”.

196/289 [489] Table 22f (erythro-2 enantiomers) examples:

[490] Optically active erythro-2 enantiomers in an enriched form [= form (2S, 3R) greater than 90% ee] which have the chemical structure of the structural formula (Iva) in the form erythro-2 [= formula (erythro-2 -lva)], where the structural combination of the groups Q, (R ¹ ) m and (R ² ) n is defined according to a line number in Table 1. The individual compounds are numbered “erythro2-lva (line number ) ”.

[491] Table 23: compounds of structural formulas (Iw), (Iwa), (Iwb), (Iwc), (Iwd), (Iwe), (Iwf), (Iwg) and (Iwh), where each groups Q, (R ¹ ) m and (R ² ) n have the meaning defined in table 1:

(Iw) (lwa) A ¹ is (= O) (lwb) A ¹ is (= S) (lwc) A ¹ is (= N-CH ₃ ) (lwd) A ¹ is (= N-OH) (lwe ) A ¹ is (= N-OCH ₃ ) (lwf) A ¹ is (= N-NH ₂ ) (lwg) A ¹ is [«N-NÍCHJJ (lwh) A ¹ is (= N-benzll) [492] Table 23, examples of erythro / threo mixtures (proportions from 70:30 to

30:70): Examples include the compounds of the respective structural formulas (Iwa) to (Iwh), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in that the meanings of the groups Q, (R ¹ ) m (R ² ) n are defined according to a line number in Table 1. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[493] Tables 23a to 23f: compounds of structural formulas (treo-lwa) and (treo20 2-lwa), in which each of the groups Q, (R ¹ ) m and (R ² ) does not have the meaning defined in table 1 :

197/289

(treo-lwa) = (treo-1-lwa) + (treo-2-lwa) (50:50) = (rac.) [494] Table 23a (treo racemates), examples:

[495] Structural formula (Iwa) compounds in the form of racemic mixture of the treo [= formula (treo-lwa)] isomers, in which the structural combination of the groups Q, (R ¹ ) m and (R ² ) n is defined according to a line number in Table 1. The individual compounds are numbered “treo-lwa (line number)”.

[496] Table 23b (optically active treo-2 compounds), examples:

[497] Optically active treo-2 enantiomers in an enriched form [= form (2R, 3R) greater than 90% ee] which have the chemical structure of the structural formula (treo-2-lwa), in which the structural combination of the groups Q, (R ¹ ) m and (R ² ) _n are defined according to a line number in Table 1. The individual compounds are numbered “treo-2-lwa (line number)”.

[498] Table 23c (optically active treo-1 enantiomers), examples:

[499] Optically active treo-1 enantiomers in an enriched form [= form (2S, 3S) greater than 90% ee] which have the chemical structure of the structural formula (treo-1-Iwa), in which the structural combination of the groups Q, (R ¹ ) m and (R ² ) _n are defined according to a line number in Table 1. The individual compounds are numbered “treo-1-lwa (line number)”.

[500] Table 23d (erythro racemates), examples:

[501] Compounds of structural formula (Iwa) in the form of a racemic mixture of erythro isomers [= formula (erythro-lwa)], where the combination

198/289 structural group Q, (R ¹ ) m (R ² ) n is defined according to a line number in Table 1. The individual compounds are numbered “erythro-Iwa (line number)”.

[502] Table 23e (erythro-1 enantiomers), examples:

[503] Optically active erythro-1 enantiomers in an enriched form [= form (2R, 3S) greater than 90% ee] which have the chemical structure of the structural formula (Iwa) in the form erythro-1 [= formula (erythro-1 -Iwa)], where the structural combination of the groups Q, (R ¹ ) m and (R ² ) n is defined according to a line number in Table 1. The individual compounds are numbered “erythro1- Iwa (line number ) ”.

[504] Table 23f (erythro-2 enantiomers) examples:

[505] Optically active erythro-2 enantiomers in an enriched form [= form (2S, 3R) greater than 90% ee] which have the chemical structure of the structural formula (Iwa) in the form erythro-2 [= formula (erythro-2 -Iwa)], where the structural combination of groups Q, (R ¹ ) m and (R ² ) n is defined according to a line number in Table 1. The individual compounds are numbered “erythro2- Iwa (line number ) ”.

[506] Table 24: compounds of structural formulas (Ix), (Ixa), (Ixb), (Ixc), (Ixd), (Ixe), (Ixf), (Ixg) and (Ixh), where each groups Q, (R ¹ ) m and (R ² ) n have the meaning defined in table 1:

[507] Table 24, examples of erythro / threo mixtures (proportions from 70:30 to

30:70): Examples include the compounds of the respective structural formulas (Ixa) to (Ixh), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in that the meanings of the groups Q, (R ¹ ) m and (R ² ) n are defined according to a line number in Table 1. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[508] Tables 24a to 24f: compounds of structural formulas (treo-Ixa) and (treo2-Ixa), in which each of the groups Q, (R ¹ ) m and (R ² ) n does not have the defined meaning

199/289 in Table 1:

(treo-lxa) = (treo-1-lxa) + (treo-2-lxa) (50:50) = (rac.) [509] Table 24a (treo racemates), examples:

[510] Compounds of structural formula (Ixa) in the form of a racemic mixture 5 of the isomers treo [= formula (treo-lxa)], where the structural combination of the groups Q, (R ¹ ) m (R ² ) n is not defined according to a line number in Table 1. The individual compounds are numbered “threo-lxa (line number)”.

[511] Table 24b (optically active treo-2 compounds), examples:

[512] Optically active treo-2 enantiomers in an enriched form [= form (2R, 3R) greater than 90% ee] which have the chemical structure of the structural formula (treo-2-lxa), in which the structural combination of the groups Q, (R ¹ ) m and (R ² ) _n are defined according to a line number in Table 1. The individual compounds are numbered “treo-2-lxa (line number)”.

[513] Table 24c (optically active treo-1 enantiomers), examples:

[514] Optically active treo-1 enantiomers in an enriched form [= form (2S, 3S) greater than 90% ee] which have the chemical structure of the structural formula (treo-1-Ixa), in which the structural combination of the groups Q, (R ¹ ) m and (R ² ) _n are defined according to a line number in Table 1. The individual compounds are numbered “treo-1-lxa (line number)”.

[515] Table 24d (erythro racemates), examples:

[516] Compounds of structural formula (Ixa) in the form of a mixture

200/289 racemic isomers erythro [= formula (erythro-Ixa)], in which the structural combination of the groups Q, (R ¹ ) m and (R ² ) n is defined according to a line number in Table 1. individual compounds are numbered “erythro-Ixa (line number)”.

[517] Table 24e (erythro-1 enantiomers), examples:

[518] Optically active erythro-1 enantiomers in an enriched form [= form (2R, 3S) greater than 90% ee] which have the chemical structure of the structural formula (Ixa) in the form erythro-1 [= formula (erythro-1 -Ixa)], where the structural combination of the groups Q, (R ¹ ) m and (R ² ) n is defined according to a line number in Table 1. The individual compounds are numbered “erythro1- Ixa (line number ) ”.

[519] Table 24f (erythro-2 enantiomers) examples:

[520] Optically active erythro-2 enantiomers in an enriched form [= form (2S, 3R) greater than 90% ee] which have the chemical structure of the structural formula (Ixa) in the form erythro-2 [= formula (erythro-2 -Ixa)], where the structural combination of groups Q, (R ¹ ) m and (R ² ) n is defined according to a line number in Table 1. The individual compounds are numbered “erythro2- Iwa (line number ) ”.

[521] Table 25: definitions of structural combinations of groups (R ¹ ) m (R ² ) n for the following tables of compounds of structural formula (I) according to the invention.

No. (R ¹ ) m (R ² ) n 1 3-F 4-Cl 2 3-F 3-F 3 3,4-F2 4-Cl 4 3-F 4-Br 5 3-Cl 3-F 6 3,4-F2 3-F 7 H 3-F 8 4-F 3-F

201/289

No. (R ¹ ) m (R ² ) n 9 3-F 3-Cl 10 3,4-F2 3-Cl 11 3-Br 3-F 12 2.5-F2 3-F 13 3-F 2-F 14 3,4,5-Fa 4-Cl 15 4-F 3-Cl 16 3,4-F2 3-F, 4-Cl 17 3,4-F2 2-F 18 3-F 2,3-F2 19 4-F 3,5-F2 20 3-F 4-F 21 3,4-F2 3-Cl, 5-F 22 3-F 3-Cl, 5-F 23 3-F 2.5-F2 24 3,4-F2 2,3-F2 25 3,4-F2 2.5-F2 26 3-Cl 3-Cl, 5-F 27 3-F, 4-Cl 3-Cl 28 3,4-F2 3-NO2 29 3,4-F2 H 30 3-Cl, 4-F 3-F 31 3,4-F2 4-OMe 32 3-F H 33 3-F 2,4-F2 34 3-F 2,6-F2 35 3-F 3,4-F2 36 3-F 3,5-F2

202/289

No. (R ¹ ) m (R ² ) n 37 3-F 2-Cl 38 3-F 2,3-Cb 39 3-F 2,4-Cb 40 3-F 3,4-Cb 41 3-F 3.5-Cb 42 3,4-F2 2,4-F2 43 3,4-F2 2,6-F2 44 3,4-F2 3,4-F2 45 3,4-F2 3,5-F2 46 3,4-F2 2,4-Cb 47 3,4-F2 2,6-Cb 48 3,4-F2 3.5-Cb 49 3-Cl H 50 3-Cl 2-F 51 3-Cl 4-F 52 3-Cl 2,3-F2 53 3-Cl 2.5-F2 54 3-Cl 2,6-F2 55 3-Cl 3,5-F2 56 3-Cl 2-Cl 57 3-Cl 3-Cl 58 3-Cl 2,3-Cb 59 3-Cl 2,4-Cb 60 3-Cl 2.5-Cb 61 3-Cl 3.5-Cb 62 3,4-Cb 2.5-F2 63 3-Cl, 4-F 3-Cl 64 3-F, 4-Cl 2,3-F2

203/289

No. (R ¹ ) m (R ² ) n 65 3-F, 4-Cl 3,5-F2 66 3,4-F2 3,4-Cb 67 3,4-F2 3.5-Cb 68 3-Cl H 69 3-Cl 2,4-F2 70 3-Cl 3,4-F2 71 3-Cl 4-Cl 72 3-Cl 2,6-Cb 73 3,4-Cb H 74 3,4-Cb 2-F 75 3,4-Cb 3-F 76 3,4-Cb 4-F 77 3,4-Cb 2,6-F2 78 3,4-Cb 3,5-F2 79 3,4-Cb 2-Cl 80 3,4-Cb 3-Cl 81 3,4-Cb 4-Cl 82 3,4-Cb 2,4-Cb 83 3,4-Cb 2.5-Cb 84 3,4-Cb 2,6-Cb 85 3,4-Cb 3,4-Cb 86 3,4-Cb 3.5-Cb 87 3-Cl, 4-F H 88 3-Cl, 4-F 2-F 89 3-Cl, 4-F 4-F 90 3-Cl, 4-F 2,3-F2 91 3-Cl, 4-F 2,4-F2 92 3-Cl, 4-F 2.5-F2

204/289

No. (R ¹ ) m (R ² ) n 93 3-Cl, 4-F 2,6-F2 94 3-Cl, 4-F 3,4-F2 95 3-Cl, 4-F 3,5-F2 96 3-Cl, 4-F 2-Cl 97 3-Cl, 4-F 3-Cl 98 3-Cl, 4-F 4-Cl 99 3-Cl, 4-F 2,3-Cb 100 3-Cl, 4-F 2,4-Cb 101 3-Cl, 4-F 2.5-Cb 102 3-Cl, 4-F 2,6-Cb 103 3-Cl, 4-F 3,4-Cb 104 3-Cl, 4-F 3.5-Cb 105 3-Cl, 4-F H 106 3-F, 4-Cl 2-F 107 3-F, 4-Cl 3-F 108 3-F, 4-Cl 4-F 109 3-F, 4-Cl 2,4-F2 110 3-F, 4-Cl 2.5-F2 111 3-F, 4-Cl 2,6-F2 112 3-F, 4-Cl 3,4-F2 113 3-F, 4-Cl 2-Cl 114 3-F, 4-Cl 4-Cl 115 3-F, 4-Cl 2,4-Cb 116 3-F, 4-Cl 2.5-Cb 117 3-F, 4-Cl 2,6-Cb 118 3-F, 4-Cl 3,4-Cb 119 3-F, 4-Cl 3.5-Cb 120 3-CN H

205/289

No. (R ¹ ) m (R ² ) n 121 3-CN 2.5-F2 122 3-CN 2,6-F2 123 3-CN 2,3-F2 124 3-CN 2,4-F2 125 3-CN 3,4-F2 126 3-CN 3,5-F2 127 3-CN 4-Cl 128 3-CN 3-Cl 129 3-CN 2-Cl 130 3-CN 4-F 131 3-CN 3-F 132 3-CN 2-F 133 2-CN 3-F 134 2-CN 4-F 135 2-CN 4-Cl 136 3-NO2 H 137 3-NO2 2.5-F2 138 3-NO2 2,6-F2 139 3-NO2 2,3-F2 140 3-NO2 2,4-F2 141 3-NO2 3,4-F2 142 3-NO2 3,5-F2 143 3-NO2 4-Cl 144 3-NO2 3-Cl 145 3-NO2 2-Cl 146 3-NO2 4-F 147 3-NO2 3-F 148 3-NO2 2-F

206/289

No. (R ¹ ) m (R ² ) n 149 H 2,6-F2 150 H 3,4-F2 151 H 3,5-F2 152 H 2,3-F2 153 H 2,4-F2 154 H 2.5-F2 155 H 2-Cl 156 H 3-Cl 157 H 4-Cl 158 H 2-F 159 H 4-F 160 H 2,3-Cb 161 H 2,4-Cb 162 H 2.5-Cb 163 H 2,6-Cb 164 H 3,4-Cb 165 H 3.5-Cb 166 3-CN, 4-F 3-F 167 3-CN, 4-F 3-Cl 168 3-CN, 4-F 3-CN 169 3-CN, 4-F 4-F 170 3-CN, 4-F 4-Cl 171 3-CN, 4-F 2.5-F2 172 3-CN, 4-F 2,6-F2 173 3-CN, 4-F 3-F 174 3-CN, 4-F 3-Cl 175 3-CN, 4-F 3-CN 176 3-CN, 4-F 4-F

207/289

No. (R ¹ ) m (R ² ) n 177 3-CN, 4-F 4-Cl 178 3-CN, 4-F 2.5-F2 179 3-CN, 4-F 2,6-F2 180 3-Br, 4-F 3-F 181 3-Br, 4-F 3-Cl 182 3-Br, 4-F 3-CN 183 3-Br, 4-F 4-F 184 3-Br, 4-F 4-Cl 185 3-Br, 4-F 2.5-F2 186 3-Br, 4-F 2,6-F2 187 3-Br, 4-F 3-F 188 3-Br, 4-F 3-Cl 189 3-Br, 4-F 3-CN 190 3-Br, 4-F 4-F 191 3-Br, 4-F 4-Cl 192 3-Br, 4-F 2.5-F2 193 3-Br, 4-F 2,6-F2 194 3-F, 4-CN 3-F 195 3-F, 4-CN 3-Cl 196 3-F, 4-CN 3-CN 197 3-F, 4-CN 4-F 198 3-F, 4-CN 4-Cl 199 3-F, 4-CN 2.5-F2 200 3-F, 4-CN 2,6-F2 201 3-F, 4-CN 3-F 202 3-F, 4-CN 3-Cl 203 3-F, 4-CN 3-CN 204 3-F, 4-CN 4-F

208/289

No. (R ¹ ) m (R ² ) n 205 3-F, 4-CN 4-Cl 206 3-F, 4-CN 2.5-F2 207 3-F, 4-CN 2,6-F2

[522] For reference purposes, specific numbers (= example numbers) have been assigned to individual compounds in Tables 26 to 35 below, where the example number in question consists of the number of the chemical formula assigned to the respective table and a “number line ”(line number) which refers to the same number in the row in the first column of Table 25. The chemical structure of example no. “(Formula number) (line number)” is thus unambiguously defined by the previous formula in the respective table by the formula number and line number in table 25, for example:

[523] example no. “IB8aa1” in Table 26 is the compound of structural formula (IB8), where R = methyl and A ¹ = O [= formula (IB8aa), see the following table of substituent-formulas for structural formula (IB8)] and (R ¹ ) m = 3-F and (R ² ) n = 4-Cl are defined according to line 1 of table 25, or a tautomer thereof;

[524] example no. “IB8af136” in Table 26 is the compound of structural formula (IB8), where R = methyl and A ¹ = N-NH2 [= formula (IB8af)] and (R ¹ ) m = 3-NO2 and (R ² ) n = H (n = 0, unsubstituted) are defined according to line 136 of table 25, or a tautomer thereof.

[525] Table 26: compounds of structural formula (IB8), in which each of the groups (R ¹ ) m and (R ² ) n has the meaning defined in table 25:

(IB8)

209/289 [526] Definition of the sub-formulas for the structural formula (IB8), with fixed R and A ¹ radicals:

Sub-formula for (IB8) R A ¹ (IB8a) CH3 A ¹ (IB8aa) CH3 O (IB8ab) CH3 s (IB8ac) CH3 = N-CH3 (IB8ad) CH3 = N-OH (IB8ae) CH3 = N-OCH3 (IB8af) CH3 = N-NH2 (IB8ag) CH3 = N-N (CH3) 2 (IB8ah) CH3 = N-CH2-C6H5 (IB8b) C2H5 A ¹ (IB8ba) C2H5 O (IB8bb) C2H5 s (IB8bc) C2H5 = N-CH3 (IB8bd) C2H5 = N-OH (IB8be) C2H5 = N-OCH3 (IB8bf) C2H5 = N-NH2 (IB8bg) C2H5 = N-N (CH3) 2 (IB8bh) C2H5 = N-CH2-C6H5 (IB8c) n-C3H7 A ¹ (IB8ca) n-C3H7 O (IB8cb) n-C3H7 s (IB8cc) n-C3H7 = N-CH3 (IB8cd) n-C3H7 = N-OH (IB8ce) n-C3H7 = N-OCH3 (IB8cf) n-C3H7 = N-NH2 (IB8cg) n-C3H7 = N-N (CH3) 2

210/289

Sub-formula for (IB8) R A ¹ (IB8ch) n-C3H7 = N-CH2-C6H5 (IB8d) i-C3H7 A ¹ (IB8da) i-C3H7 O (IB8db) i-C3H7 s (IB8dc) i-C3H7 = N-CH3 (IB8dd) i-C3H7 = N-OH (IB8de) i-C3H7 = N-OCH3 (IB8df) i-C3H7 = N-NH2 (IB8dg) i-C3H7 = N-N (CH3) 2 (IB8dh) i-C3H7 = N-CH2-C6H5

[527] Table 26, examples of erythro / threo mixtures (proportions from 70:30 to 30:70):

[528] Examples include the compounds of the respective structural formulas (IB8aa) to (IB8ah), (IB8ba) to (IB8bh), (IB8ca) to (IB8ch) and (IB8da) to (IB8dh), in each case under the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in which the meanings of groups (R ¹ ) m and (R ² ) n are defined according to a line number in table 25. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[529] Tables 26a to 26f: compounds of structural formulas (treo-IB8), (treo-1IB8) and (treo-2-IB8), in which each of the groups (R ¹ ) m and (R ² ) does not have the meaning

211/289

(treo-IB8) = (treo-1-IB8) + (treo-2-IB8) (50:50) = (rac.) [530] Definition of the sub-formulas for the structural formulas treo- (IB8), treo1 - (IB8) and treo-2- (IB8), with fixed R and A ¹ radicals:

Sub-formula R A ¹ Stereochemistry treo- (IB8a) ch ₃ A ¹ (2S, 3S) / (2R, 3R), racemic treo-1- (IB8a) ch ₃ A ¹ (2S, 3S), optically active treo-2- (IB8a) ch ₃ A ¹ (2R, 3R), optically active treo- (IB8aa) ch ₃ 0 (2S, 3S) / (2R, 3R), racemic treo-1- (IB8aa) ch ₃ 0 (2S, 3S), optically active treo-2- (IB8aa) ch ₃ 0 (2R, 3R), optically active treo- (IB8b) C2H5 A ¹ (2S, 3S) / (2R, 3R), racemic treo-1- (IB8b) C2H5 A ¹ (2S, 3S), optically active treo-2- (IB8b) C2H5 A ¹ (2R, 3R), optically active treo- (IB8ba) C2H5 0 (2S, 3S) / (2R, 3R), racemic treo-1- (IB8ba) C2H5 0 (2S, 3S), optically active treo-2- (IB8ba) C2H5 0 (2R, 3R), optically active treo- (IB8c) nC ₃ H7 A ¹ (2S, 3S) / (2R, 3R), racemic treo-1- (IB8c) nC ₃ H7 A ¹ (2S, 3S), optically active treo-2- (IB8c) nC ₃ H7 A ¹ (2R, 3R), optically active treo- (IB8ca) nC ₃ H7 0 (2S, 3S) / (2R, 3R), racemic treo-1- (IB8ca) nC ₃ H7 0 (2S, 3S), optically active treo-2- (IB8ca) nC ₃ H7 0 (2R, 3R), optically active

212/289

Sub-formula R A ¹ Stereochemistry treo- (IB8d) i-C3H7 A ¹ (2S, 3S) / (2R, 3R), racemic treo-1- (IB8d) i-C3H7 A ¹ (2S, 3S), optically active treo-2- (IB8d) i-C3H7 A ¹ (2R, 3R), optically active treo- (IB8da) i-C3H7 O (2S, 3S) / (2R, 3R), racemic treo-1- (IB8da) i-C3H7 O (2S, 3S), optically active treo-2- (IB8da) i-C3H7 O (2R, 3R), optically active

[531] Table 26a (trematite racemates), examples:

[532] Compounds of structural formulas treo- (IB8aa), treo- (IB8ba), treo- (IB8ca) and treo- (IB8da), in each case in the form of a racemic mixture of the treo isomers, in which the structural combination of groups (R ¹ ) m and (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “treo-IB8aa (line number)”, “treo-IB8ba (line number)” , “TreoIB8ca (line number)” and “treo-IB8da (line number)”.

[533] Table 26b (optically active treo-2 compounds), examples:

[534] Compounds of structural formulas treo-2- (IB8aa), treo-2- (IB8ba), treo-210 (IB8ca) and treo-2- (IB8da), in each case in a stereochemically enriched form [= form (2R , 3R) greater than 90% ee], where the structural combination of the groups (R ¹ ) m and (R ² ) n is defined according to a row number in Table 25. The individual compounds are numbered “treo-2 -IB8aa (line number) ”,“ treo-2-IB8ba (line number) ”,“ treo-2-IB8ca (line number) ”and“ treo-2-IB8da (line number) ”.

[535] Table 26c (optically active treo-1 enantiomers), examples:

[536] Optically active enantiomeric compounds of structural formulas treo-1- (IB8aa), treo-1- (IB8ba), treo-1- (IB8ca) and treo-1- (IB8da), in each case in a stereochemically enriched form [ = form (2S, 3S) greater than 90% ee], where the structural combination of the groups (R ¹ ) m and (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “Treo-1-IB8aa (line number)”, “treo-1-IB8ba (line number)”, “treo-1-IB8ca (line number)” and “treo-1-IB8da (line number) ”.

213/289 [537] Table 26d (erythro racemates), examples:

[538] Compounds of structural formulas erythro- (IB8aa), erythro- (IB8ba), erythro (IB8ca) and erythro- (IB8da), in each case in the form of a racemic mixture of erythro isomers, in which the structural combination of groups (R ¹ ) m (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “erythro-IB8aa (line number)”, “erythro-IB8ba (line number)” , “Eritro-IB8ca (line number)” and “eritro-IB8da (line number)”.

[539] Table 26e (erythro-1 enantiomers), examples:

[540] Optically active enantiomeric compounds of structural formulas 10 erythro-1- (IB8aa), erythro-1- (IB8ba), erythro-1- (IB8ca) and erythro-1- (IB8da), in each case in a stereochemically enriched form [= form (2R, 3S) greater than 90% ee], where the structural combination of groups (R ¹ ) m and (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “eritro-1-IB8aa (line number)”, “eritro-1-IB8ba (line number)”, “eritro-1-IB8ca (line number)” and “eritro-1-IB8da (line number) ) ”.

[541] Table 26f (erythro-2 enantiomers) examples:

[542] Optically active enantiomeric compounds of structural formulas erythro-2- (IB8aa), erythro-2- (IB8ba), erythro-2- (IB8ca) and erythro-2- (IB8da), in each case in a stereochemically enriched form [ = shape (2S, 3R) greater than

90% ee], where the structural combination of the groups (R ¹ ) m and (R ² ) n is defined according to a row number in Table 25. The individual compounds are numbered “erythro-2-IB8aa (number of line) ”,“ erythro-2-IB8ba (line number) ”,“ erythro-2-IB8ca (line number) ”and“ erythro-2-IB8da (line number) ”.

[543] Table 27: compounds of structural formula (IBX), in which each of the groups (R ¹ ) m and (R ² ) n has the meaning defined in table 25:

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(IBX) [544] Definitions of the sub-formulas for the structural formula (IBX) with fixed R and A ¹ radicals:

Sub-formula for (IBX) R A ¹ (IBXa) CH3 A ¹ (IBXaa) CH3 O (IBXab) CH3 s (IBXac) CH3 = N-CH3 (IBXad) CH3 = N-OH (IBXae) CH3 = N-OCH3 (IBXaf) CH3 = N-NH2 (IBXag) CH3 = N-N (CH3) 2 (IBXah) CH3 = N-CH2-C6H5 (IBXb) C2H5 A ¹ (IBXba) C2H5 O (IBXbb) C2H5 s (IBXbc) C2H5 = N-CH3 (IBXbd) C2H5 = N-OH (IBXbe) C2H5 = N-OCH3 (IBXbf) C2H5 = N-NH2 (IBXbg) C2H5 = N-N (CH3) 2 (IBXbh) C2H5 = N-CH2-C6H5 (IBXc) n-C3H7 A ¹ (IBXca) n-C3H7 O

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Sub-formula for (IBX) R A ¹ (IBXcb) n-C3H7 s (IBXcc) n-C3H7 = N-CH3 (IBXcd) n-C3H7 = N-OH (IBXce) n-C3H7 = N-OCH3 (IBXcf) n-C3H7 = N-NH2 (IBXcg) n-C3H7 = N-N (CH3) 2 (IBXch) n-C3H7 = N-CH2-CgH5 (IBXd) i-C3H7 A ¹ (IBXda) i-C3H7 O (IBXdb) i-C3H7 s (IBXdc) i-C3H7 = N-CH3 (IBXdd) i-C3H7 = N-OH (IBXde) i-C3H7 = N-OCH3 (IBXdf) i-C3H7 = N-NH2 (IBXdg) i-C3H7 = N-N (CH3) 2 (IBXdh) i-C3H7 = N-CH2-C6H5

[545] Table 27, examples of erythro / threo mixtures (proportions from 70:30 to 30:70):

[546] Examples include the compounds of the respective structural formulas (IBXaa) to (IBXah), (IBXba) to (IBXbh), (IBXca) to (IBXch) and (IBXda) to (IBXdh), in each case under in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in which the meanings of groups (R ¹ ) m and (R ² ) n are as defined according to a line number in the Table 25, Individual compounds are numbered “(formula) (line number)”, without any parentheses.

[547] Tables 27a to 27f: compounds of structural formulas (treo-IBX), (treo-1IBX) and (treo-2-IBX), in which each of the groups (R ¹ ) m and (R ² ) does not have the meaning defined in table 25:

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(treo-IBX) = (treo-1-ΙΒΧ) + (treo-2-ΙΒΧ) (50:50) = (rac.) [548] Definitions of the sub-formulas for the structural formulas treo- (IBX), treo1 - (IBX) and treo-2- (IBX) with fixed ReA ¹ radicals:

Sub-formula R A ¹ Stereochemistry treo- (IBXa) ch ₃ A ¹ (2S, 3S) / (2R, 3R), racemic treo-l- (IBXa) ch ₃ A ¹ (2S, 3S), optically active treo-2- (IBXa) ch ₃ A ¹ (2R, 3R), optically active treo- (IBXaa) ch ₃ 0 (2S, 3S) / (2R, 3R), racemic treo-l- (IBXaa) ch ₃ 0 (2S, 3S), optically active treo-2- (IBXaa) ch ₃ 0 (2R, 3R), optically active treo- (IBXb) C2H5 A ¹ (2S, 3S) / (2R, 3R), racemic treo-l- (IBXb) C2H5 A ¹ (2S, 3S), optically active treo-2- (IBXb) C2H5 A ¹ (2R, 3R), optically active treo- (IBXba) C2H5 0 (2S, 3S) / (2R, 3R), racemic treo-l- (IBXba) C2H5 0 (2S, 3S), optically active treo-2- (IBXba) C2H5 0 (2R, 3R), optically active treo- (IBXc) nC ₃ H7 A ¹ (2S, 3S) / (2R, 3R), racemic treo-l- (IBXc) nC ₃ H7 A ¹ (2S, 3S), optically active treo-2- (IBXc) nC ₃ H7 A ¹ (2R, 3R), optically active treo- (IBXca) nC ₃ H7 0 (2S, 3S) / (2R, 3R), racemic treo-l- (IBXca) nC ₃ H7 0 (2S, 3S), optically active treo-2- (IBXca) nC ₃ H7 0 (2R, 3R), optically active

217/289

Sub-formula R A ¹ Stereochemistry treo- (IBXd) i-C3H7 A ¹ (2S, 3S) / (2R, 3R), racemic treo-1- (IBXd) i-C3H7 A ¹ (2S, 3S), optically active treo-2- (IBXd) i-C3H7 A ¹ (2R, 3R), optically active treo- (IBXda) i-C3H7 O (2S, 3S) / (2R, 3R), racemic treo-1- (IBXda) i-C3H7 O (2S, 3S), optically active treo-2- (IBXda) i-C3H7 O (2R, 3R), optically active

[549] Table 27a (trematous racemates), examples:

[550] Compounds of structural formulas treo- (IBXaa), treo- (IBXba), treo (IBXca) and treo- (IBXda), in each case in the form of a racemic mixture of the treo isomers, in which the structural combination of the groups (R ¹ ) m and (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “treo-IBXaa (line number)”, “treo-IBXba (line number)”, “Treo-IBXca (line number)” and “treo-IBXda (line number)”.

[551] Table 27b (optically active treo-2 compounds), examples:

[552] Compounds of structural formulas treo-2- (IBXaa), treo-2- (IBXba), treo-210 (IBXca) and treo-2- (IBXda), in each case in a stereochemically enriched form [= form (2R , 3R) greater than 90% ee], where the structural combination of the groups (R ¹ ) m and (R ² ) n is defined according to a row number in Table 25. The individual compounds are numbered “treo-2 -IBXaa (line number) "," treo-2-IBXba (line number) "," treo-2-IBXca (line number) "and" treo-2-IBXda (line number) ".

[553] Table 27c (optically active treo-1 enantiomers), examples:

[554] Optically active enantiomeric compounds of structural formulas treo-1- (IBXaa), treo-1- (IBXba), treo-1- (IBXca) and treo-1- (IBXda), in each case in a stereochemically enriched form [ = form (2S, 3S) greater than 90% ee], where the structural combination of the groups (R ¹ ) m and (R ² ) n is defined according to a row number in Table 25. The individual compounds are numbered “Treo-1-IBXaa (line number)”, “treo-1-IBXba (line number)”, “treo-1-IBXca (line number)” and “treo-1-IBXda (line number) ”.

218/289 [555] Table 27d (erythro racemates), examples:

[556] Compounds of structural formulas erythro- (IBXaa), erythro- (IBXba), erythro (IBXca) and erythro- (IBXda), in each case in the form of racemic mixture of the threus isomers, in which the structural combination of the groups (R ¹ ) m (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “erythro-IBXaa (line number)”, “erythroIBXba (line number)”, “erythro -IBXca (line number) ”and“ erythro-IBXda (line number) ”.

[557] Table 27e (erythro-1 enantiomers), examples:

[558] Optically active enantiomeric compounds of structural formulas erythro-1- (IBXaa), erythro-1- (IBXba), erythro-1- (IBXca) and erythro-1- (IBXda), in each case in a stereochemically enriched form [ = form (2R, 3S) greater than 90% ee], where the structural combination of groups (R ¹ ) m and (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “Erythro-1-IBXaa (line number)”, “erythro-1-IBXba (line number)”, “erythro-1-IBXca (line number)” and “erythro-1-IBXda (line number) ”.

[559] Table 27f (erythro-2 enantiomers) examples:

[560] Optically active enantiomeric compounds of structural formulas erythro-2- (IBXaa), erythro-2- (IBXba), erythro-2- (IBXca) and erythro-2- (IBXda), in each case in a stereochemically enriched form [ = form (2S, 3R) greater than 90% ee], where the structural combination of the groups (R ¹ ) m and (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “Erythro-2-IBXaa (line number)”, “erythro-2-IBXba (line number)”, “erythro-2-IBXca (line number)” and “erythro-2-IBXda (line number) ”.

[561] Table 28: compounds of structural formula (IB9), where each of the groups (R ¹ ) m and (R ² ) n has the meaning defined in table 25:

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(IB9) [562] Definitions of sub-formulas for structural formula (IB9) with fixed R and A ¹ radicals:

Sub-formula for (IB9) R A ¹ (IB9a) CH3 A ¹ (IB9aa) CH3 O (IB9ab) CH3 s (IB9ac) CH3 = N-CH3 (IB9ad) CH3 = N-OH (IB9ae) CH3 = N-OCH3 (IB9af) CH3 = N-NH2 (IB9ag) CH3 = N-N (CH3) 2 (IB9ah) CH3 = N-CH2-C6H5 (IB9b) C2H5 A ¹ (IB9ba) C2H5 O (IB9bb) C2H5 s (IB9bc) C2H5 = N-CH3 (IB9bd) C2H5 = N-OH (IB9be) C2H5 = N-OCH3 (IB9bf) C2H5 = N-NH2 (IB9bg) C2H5 = N-N (CH3) 2 (IB9bh) C2H5 = N-CH2-C6H5 (IB9c) n-C3H7 A ¹

220/289

Sub-formula for (IB9) R A ¹ (IB9ca) n-C3H7 O (IB9cb) n-C3H7 s (IB9cc) n-C3H7 = N-CH3 (IB9cd) n-C3H7 = N-OH (IB9ce) n-C3H7 = N-OCH3 (IB9cf) n-C3H7 = N-NH2 (IB9cg) n-C3H7 = N-N (CH3) 2 (IB9ch) n-C3H7 = N-CH2-C6H5 (IB9d) i-C3H7 A ¹ (IB9da) i-C3H7 O (IB9db) i-C3H7 s (IB9dc) i-C3H7 = N-CH3 (IB9dd) i-C3H7 = N-OH (IB9de) i-C3H7 = N-OCH3 (IB9df) i-C3H7 = N-NH2 (IB9dg) i-C3H7 = N-N (CH3) 2 (IB9dh) i-C3H7 = N-CH2-C6H5 [563] Table 27, examples of mis erythro / treus structures (proportions from 70:30 to

30:70):

[564] Examples include the compounds of the respective structural formulas (IB9aa) to (IB9ah), (IB9ba) to (IB9bh), (IB9ca) to (IB9ch) and (IB9da) to (IB9dh), in each case under the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in which the meanings of groups (R ¹ ) m and (R ² ) n are defined according to a line number in Table 25. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[565] Tables 28a to 28f: compounds of structural formulas (treo-IB9), (treo-1IB9) and (treo-2-IB9), in which each of the groups (R ¹ ) m and (R ² ) does not have the meaning defined in table 25:

221/289

(treo-IB9) = (treo-l-JB9) + (treo-2-IB9) (50:50) = (rac.) [566] Subformulas definitions for structural formulas treo- (IB9), treo1 - (IB9) and treo-2- (IB9), with fixed R and A ¹ radicals:

Sub-formula R A ¹ Stereochemistry treo- (IB9a) ch ₃ A ¹ (2S, 3S) / (2R, 3R), racemic treo-1- (IB9a) ch ₃ A ¹ (2S, 3S), optically active treo-2- (IB9a) ch ₃ A ¹ (2R, 3R), optically active treo- (IB9aa) ch ₃ 0 (2S, 3S) / (2R, 3R), racemic treo-1- (IB9aa) ch ₃ 0 (2S, 3S), optically active treo-2- (IB9aa) ch ₃ 0 (2R, 3R), optically active treo- (IB9b) C2H5 A ¹ (2S, 3S) / (2R, 3R), racemic treo-1- (IB9b) C2H5 A ¹ (2S, 3S), optically active treo-2- (IB9b) C2H5 A ¹ (2R, 3R), optically active treo- (IB9ba) C2H5 0 (2S, 3S) / (2R, 3R), racemic treo-1- (IB9ba) C2H5 0 (2S, 3S), optically active treo-2- (IB9ba) C2H5 0 (2R, 3R), optically active treo- (IB9c) nC ₃ H7 A ¹ (2S, 3S) / (2R, 3R), racemic treo-1- (IB9c) nC ₃ H7 A ¹ (2S, 3S), optically active treo-2- (IB9c) nC ₃ H7 A ¹ (2R, 3R), optically active treo- (IB9ca) nC ₃ H7 0 (2S, 3S) / (2R, 3R), racemic treo-1- (IB9ca) nC ₃ H7 0 (2S, 3S), optically active treo-2- (IB9ca) nC ₃ H7 0 (2R, 3R), optically active

222/289

Sub-formula R A ¹ Stereochemistry treo- (IB9d) i-C3H7 A ¹ (2S, 3S) / (2R, 3R), racemic treo-1- (IB9d) i-C3H7 A ¹ (2S, 3S), optically active treo-2- (IB9d) i-C3H7 A ¹ (2R, 3R), optically active treo- (IB9da) i-C3H7 O (2S, 3S) / (2R, 3R), racemic treo-1- (IB9da) i-C3H7 O (2S, 3S), optically active treo-2- (IB9da) i-C3H7 O (2R, 3R), optically active

[567] Table 28a (trematous racemates), examples:

[568] Compounds of structural formulas treo- (IB9aa), treo- (IB9ba), treo- (IB9ca) and treo- (IB9da), in each case in the form of a racemic mixture of the treo isomers, in which the structural combination of groups (R ¹ ) m (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “treo-IB9aa (line number)”, “treo-IB9ba (line number)” , “TreoIB9ca (line number)” and “treo-IB9da (line number)”.

[569] Table 28b (optically active treo-2 compounds), examples:

[570] Compounds of structural formulas treo-2- (IB9aa), treo-2- (IB9ba), treo-210 (IB9ca) and treo-2- (IB9da), in each case in a stereochemically enriched form [= form (2R , 3R) greater than 90% ee], where the structural combination of the groups (R ¹ ) m and (R ² ) n is defined according to a row number in Table 25. The individual compounds are numbered “treo-2 -IB9aa (line number) ”,“ treo-2-IB9ba (line number) ”,“ treo-2-IB9ca (line number) ”and“ treo-2-IB9da (line number) ”.

[571] Table 28c (optically active treo-1 enantiomers), examples:

[572] Optically active enantiomeric compounds of structural formulas treo-1- (IB9aa), treo-1- (IB9ba), treo-1- (IB9ca) and treo-1- (IB9da), in each case in a stereochemically enriched form [ = form (2S, 3S) greater than 90% ee], where the structural combination of the groups (R ¹ ) m and (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “Treo-1-IB9aa (line number)”, “treo-1-IB9ba (line number)”, “treo-1-IB9ca (line number)” and “treo-1-IB9da (line number) ”.

223/289 [573] Table 28d (erythro racemates), examples:

[574] Compounds of structural formulas erythro- (IB9aa), erythro- (IB9ba), erythro (IB9ca) and erythro- (IB9da), in each case in the form of racemic mixture of the threus isomers, in which the structural combination of groups (R ¹ ) m (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “erythro-IB9aa (line number)”, “erythro-IB9ba (line number)”, “Eritro-IB9ca (line number)” and “eritro-IB9da (line number)”.

[575] Table 28e (erythro-1 enantiomers), examples:

[576] Optically active enantiomeric compounds of structural formulas 10 of the individual compounds erythro-1- (IB9aa), erythro-1- (IB9ba), erythro-1- (IB9ca) and erythro-1- (IB9da), in each case in one stereochemically enriched form [= form (2R, 3S) greater than 90% ee], where the structural combination of the groups (R ¹ ) m and (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “erythro-1-IB9aa (line number)”, “erythro-1-IB9ba (line number)”, “erythro-1-IB9ca (line number)” and “erythro-1IB9da (number of line)".

[577] Table 28f (erythro-2 enantiomers) examples:

[578] Optically active enantiomeric compounds of structural formulas erythro-2- (IB9aa), erythro-2- (IB9ba), erythro-2- (IB9ca) and erythro-2- (IB9da), in each case in a stereochemically enriched form [ = form (2S, 3R) greater than 90% ee], where the structural combination of the groups (R ¹ ) m and (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “Erythro-2-IB9aa (line number)”, “erythro-2-IB9ba (line number)”, “erythro-2-IB9ca (line number)” and “erythro-2-IB9da (line number) ”.

[579] Table 29: compounds of structural formulas (IB10a), (IB10aa), (IB10ab), (IB10ac), (IB10ad), (IB10ae), (IB10af), (IB10ag) and (IB10ah), in which each groups (R ¹ ) m and (R ² ) n have the meaning defined in table 25:

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(IB10a) (IBIOaa) A ¹ is (= O) (IBIOab) A ¹ is (= S) (IBIOac) A ¹ is (= N-CH3) (IB1Oad) A ¹ is (= N-OH) (IB1Oae) A ¹ is ^ N-OCHj) (IB10af) A ¹ is (= N-NH2) (IB10ag) A ¹ is [= NN (CH ₃ ) 2] (IBIOah) A ¹ is (= N-benzyl) [580] Table 29, examples of erythro / threo mixtures (proportions from 70:30 to

30:70): Examples include the compounds of the respective structural formulas (IB10aa) to (IB10ah), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in that the meanings of the groups (R ¹ ) m (R ² ) n are defined according to a line number in Table 25. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[581] Tables 29a to 29f: compounds of structural formulas (treo-IB10aa) and (treo-2-IB10aa), in which each of the groups (R ¹ ) m and (R ² ) does not have the meaning defined in table 25:

N-0 ^ Ll

(treo-1-IBIOaa) (treo-2-IB10aa) (treo-lB10aa) = (treo-1-IB10aa) + (treo-2-IB10aa) (50:50) = (rac.) [582] Table 29a (treo racemates), examples:

[583] Compounds of structural formula (IB10aa) in the form of a mixture

225/289 racemic isomer of treo [= formula (treo-IB10aa)], in which the structural combination of the groups Q, (R ¹ ) m and (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “treoIB10aa (line number)”.

[584] Table 29b (optically active treo-2 compounds), examples:

[585] Optically active treo-2 enantiomers in an enriched form [= form (2R, 3R) greater than 90% ee] which have the chemical structure of the structural formula (treo-2-IB10aa), in which the structural combination of the groups Q, (R ¹ ) m (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “treo-2-IB10aa (line number)”.

[586] Table 29c (optically active treo-1 enantiomers), examples:

[587] Optically active treo-1 enantiomers in an enriched form [= form (2S, 3S) greater than 90% ee] which have the chemical structure of the structural formula (treo-1-IB10aa), in which the structural combination of the groups Q, (R ¹ ) m (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “treo-1-IB10aa (line number)”.

[588] Table 29d (erythro racemates), examples:

[589] Compounds of structural formula (IB10aa) in the form of a racemic mixture of erythro isomers [= formula (erythro-IB10aa)], where the structural combination of groups Q, (R ¹ ) m (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “eritroIB10aa (line number)”.

[590] Table 29e (erythro-1 enantiomers), examples:

[591] Optically active erythro-1 enantiomers in an enriched form [= form (2R, 3S) greater than 90% ee] which have the chemical structure of the structural formula (IB10aa) in the form erythro-1 [= formula (erythro-1 -IB10aa)], where the structural combination of groups Q, (R ¹ ) m and (R ² ) n is defined according to a row number in Table 25. The individual compounds are numbered “erythro-1-IB10aa (number of line)".

[592] Table 29f (erythro-2 enantiomers) examples:

226/289 [593] Optically active erythro-2 enantiomers in an enriched form [= form (2S, 3R) greater than 90% ee] which have the chemical structure of the structural formula (IB10aa) in erythro-2 form [= formula ( erythro-2-IB10aa)], where the structural combination of the groups Q, (R ¹ ) m and (R ² ) n is defined according to a line number in Table 25. The numbering is “erythro-2-IB10aa ( line number) ”.

[594] Table 30: compounds of structural formulas (IB10b), (IB10bb), (IB10bb), (IB10bc), (IB10bd), (IB10bf), (IB10bf), (IB10bg) and (IB10bh), where each groups (R ¹ ) m and (R ² ) n have the meaning defined in table 25.

N-0

(IB10b) (IB10ba) A ¹ is (= O) (IB10bb) A ¹ is <= S) (IB10bc) A ¹ is (= N-CH3) (IB10bd) A ¹ is (= N-OH) (IB10be) A ¹ is (= N-OCH3) (IB10bf) A ¹ is (= N-NH2) (IB10bg) A ¹ is [= NN (CH3) ₂ ] (IB10bh) A ¹ is (= N-benzyl) [595] Table 30, examples of erythro / threo mixtures (proportions from 70:30 to 30:70):

[596] Examples include the compounds of the respective structural formulas (IB10ba) to (IB10bh), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in which the meanings of groups (R ¹ ) m (R ² ) n are defined according to a line number in Table 25. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[597] Tables 30a to 30f: compounds of structural formulas (treo-IB10ba) and (treo-2-IB10ba), in which each of the groups (R ¹ ) me (R ² ) does not have the meaning defined in table 25:

227/289

(treo-IB10ba) = (treo-1-IB1 Oba) + (treo-2-IB10ba) (50:50) = (rac.) [598] Table 30a (treo racemates), examples:

[599] Structural formula compounds (IB10ba) in the form of a racemic mixture of the treo [= formula (treo-lB1 Oba)], in which the structural combination of the groups Q, (R ¹ ) m and (R ² ) n is not defined according to a line number in Table 25. The individual compounds are numbered “treoIB10ba (line number)”.

[600] Table 30b (optically active treo-2 compounds), examples:

[601] Optically active treo-2 enantiomers in an enriched form [= form (2R, 3R) greater than 90% ee] which have the chemical structure of the structural formula (treo-2-IB10ba), in which the structural combination of the groups Q, (R ¹ ) m (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “treo-2-IB10ba (line number)”.

[602] Table 30c (optically active treo-1 enantiomers), examples:

[603] Optically active treo-1 enantiomers in an enriched form [= form (2S, 3S) greater than 90% ee] which have the chemical structure of the structural formula (treo-1-IB10ba), in which the structural combination of the groups Q, (R ¹ ) m (R ² ) _n is defined according to a line number in Table 25. The individual compounds are numbered “treo-1 -IB10ba (line number)”.

[604] Table 30d (erythro racemates), examples:

[605] Compounds of structural formula (IB10ba) in the form of a mixture

228/289 racemic isomers erythro [= formula (erythro-IB10ba)], in which the structural combination of groups Q, (R ¹ ) m and (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “eritroIB10ba (line number)”.

[606] Table 30e (erythro-1 enantiomers), examples:

[607] Optically active erythro-1 enantiomers in an enriched form [= form (2R, 3S) greater than 90% ee] which have the chemical structure of the structural formula (IB10ba) in the form erythro-1 [= formula (erythro-1 -IB10ba)], where the structural combination of groups Q, (R ¹ ) m and (R ² ) n is defined according to a row number in Table 25. The individual compounds are numbered “erythro-1 -IB10ba (number of line)".

[608] Table 30f (erythro-2 enantiomers) examples:

[609] Optically active erythro-2 enantiomers in an enriched form [= form (2S, 3R) greater than 90% ee] which have the chemical structure of the structural formula (IB10ba) in the form erythro-2 [= formula (erythro-2 -IB10ba)], where the structural combination of groups Q, (R ¹ ) m and (R ² ) n is defined according to a row number in Table 25. The individual compounds are numbered “erythro-2-IB10ba (number of line)".

[610] Table 31: compounds of structural formulas (IB10c), (IB10ca), (IB10cb), (IB10cc), (IB10cd), (IB10ce), (IB1 Ocf), (IB10cg) and (IB10ch), in which each one of the groups (R ¹ ) m and (R ² ) n has the meaning defined in table 25:

(R ¹ l

N-0

(IB10c) (IB10ca) A ¹ is (= O) (IB10cb) A ¹ is (= S) (IB10cc) A ¹ is (= N-CH3) (IB10cd) A ¹ is (= N-OH) (IB10ce) A ¹ is (= N-OCH3) (IB10cf) A ¹ is (= N-NH2) (IB10cg) A ¹ is [= NN (CH3) ₂ ] (IB10ch) A ¹ is (= N-benzyl)

229/289 [611] Table 31, examples of erythro / threo mixtures (proportions from 70:30 to 30:70):

[612] Examples include the compounds of the respective structural formulas (IB10ca) to (IB10ch), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in which the meanings of groups (R ¹ ) m (R ² ) n are defined according to a line number in Table 25. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[613] Tables 31a to 31f: compounds of structural formulas (treo-IB10ca) and (treo-2-IB10ca), in which each of the groups (R ¹ ) me (R ² ) does not have the meaning defined in table 25:

(treo-IB10ca) = (treo-1-IB1 Oca) + (treo-2-IB1 Oca) (50:50) = (rac.) [614] Table 31a (treo racemates), examples:

[615] Structural formula compounds (IB10ca) in the form of a racemic mixture of the treo [= formula (treo-IB10ca)], in which the structural combination of the groups Q, (R ¹ ) m (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “treoIB10ca (line number)”.

[616] Table 31b (optically active treo-2 compounds), examples:

[617] Optically active treo-2 enantiomers in an enriched form [= form (2R, 3R) greater than 90% ee] which have the chemical structure of the structural formula (treo-2-IB10ca), in which the structural combination of the groups Q, (R ¹ ) m

230/289 and (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “treo-2-IB10ca (line number)”.

[618] Table 31c (optically active treo-1 enantiomers), examples:

[619] Treo-1 optically active enantiomers in an enriched form [= form (2S, 3S) greater than 90% ee] which have the chemical structure of the structural formula (treo-1-IB10ca), in which the structural combination of the groups Q, (R ¹ ) m and (R ² ) n are defined according to a line number in Table 25. The individual compounds are numbered “treo-1-IB10ca (line number)”.

[620] Table 31d (erythro racemates), examples:

[621] Compounds of structural formula (IB10ca) in the form of a racemic mixture of erythro isomers [= formula (erythro-IB10ca)], where the structural combination of groups Q, (R ¹ ) m and (R ² ) n defined according to a line number in Table 25. The individual compounds are numbered “eritroIB10ca (line number)”.

[622] Table 31e (erythro-1 enantiomers), examples:

[623] Optically active erythro-1 enantiomers in an enriched form [= form (2R, 3S) greater than 90% ee] which have the chemical structure of the structural formula (IB10ca) in the form erythro-1 [= formula (erythro-1 -IB10ca)], where the structural combination of groups Q, (R ¹ ) m and (R ² ) n is defined according to a row number in Table 25. The individual compounds are numbered “erythro-1-IB10ca (number of line)".

[624] Table 31f (erythro-2 enantiomers) examples:

[625] Optically active erythro-2 enantiomers in an enriched form [= form (2S, 3R) greater than 90% ee] which have the chemical structure of the structural formula (IB10ca) in form erythro-2 [= formula (erythro-2 -IB10ca)], where the structural combination of groups Q, (R ¹ ) m and (R ² ) n is defined according to a row number in Table 25. The individual compounds are numbered “erythro-2-IB10ca (number of line)".

[626] Table 32: compounds of structural formulas (IB10d), (IB10da), (IB10db), (IB10dc), (IB10dd), (IB10de), (IB10df), (IB10dg) and (IB10dh), where

231/289 each of the groups (R ¹ ) m and (R ² ) n has the meaning defined in table 25:

H ₃ C-CH _r C _s N-0 \ // X. (IB10d) -ch ₃ (IB10da) A ¹ is (= O) (R ¹ ) _m —í J θ L I ^a ' ch ₃ (IB10db) A ¹ is (= S) (IB10dc) A ¹ is (= N-CH ₃ ) ( ^R? ) _N (IB10dd) A ¹ is (= N-OH) CN kjk (IB10de) A ¹ is (= N-OCH ₃ ) (IBIOdf) A ¹ is UN-NHJ (IB10dg) A ¹ is [= NN (CH ₃ ) ₂ ] (IBIOdh) A ¹ is (= N-benzyl) [627] Table 32, examples of mixtures erythro / treus (proportions from 70:30 to

30:70):

[628] Examples include the compounds of the respective structural formulas (IB10da) to (IBIOdh), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in which the meanings of groups (R ¹ ) m (R ² ) n are defined according to a line number in Table 25. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[629] Tables 32a to 32f: compounds of structural formulas (treo-IB10da) and (treo-2-IB10da), in which each of the groups (R ¹ ) me (R ² ) does not have the meaning defined in table 25:

(treo-IB10da) = (treo-1-IB1 Oda) + (treo-2-IB1 Oda) (50:50) = (rac.)

232/289 [630] Table 32a (trematite racemates), examples:

[631] Structural formula compounds (IB10da) in the form of a racemic mixture of the treo [= formula (treo-IB10da)], in which the structural combination of the groups Q, (R ¹ ) m (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “treoIB10da (line number)”.

[632] Table 32b (optically active treo-2 compounds), examples:

[633] Optically active treo-2 enantiomers in an enriched form [= form (2R, 3R) greater than 90% ee] which have the chemical structure of the structural formula (treo-2-IB10da), in which the structural combination of the groups Q, (R ¹ ) m (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “treo-2-IB10da (line number)”.

[634] Table 32c (optically active treo-1 enantiomers), examples:

[635] Optically active treo-1 enantiomers in an enriched form [= form (2S, 3S) greater than 90% ee] which have the chemical structure of the structural formula (treo-1-IB10da), in which the structural combination of the groups Q, (R ¹ ) m and (R ² ) n are defined according to a line number in Table 25. The individual compounds are numbered “treo-1-IB10da (line number)”.

[636] Table 32d (erythro racemates), examples:

[637] Compounds of structural formula (IB10da) in the form of a racemic mixture of erythro isomers [= formula (erythro-IB10da)], in which the structural combination of groups Q, (R ¹ ) m (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “eritroIB10da (line number)”.

[638] Table 32e (erythro-1 enantiomers), examples:

[639] Optically active erythro-1 enantiomers in an enriched form [= form (2R, 3S) greater than 90% ee] which have the chemical structure of the structural formula (IB10da) in the form erythro-1 [= formula (erythro-1 -IB10da)], where the structural combination of groups Q, (R ¹ ) m and (R ² ) n is defined according to a row number in Table 25. The individual compounds are numbered

233/289 “eritro-1 -IB10da (line number)”.

[640] Table 32f (erythro-2 enantiomers) examples:

[641] Optically active erythro-2 enantiomers in an enriched form [= form (2S, 3R) greater than 90% ee] which have the chemical structure of the structural formula (IB10da) in the form erythro-2 [= formula (erythro-2 -IB10da)], where the structural combination of groups Q, (R ¹ ) m and (R ² ) n is defined according to a row number in Table 25. The individual compounds are numbered “erythro-2-IB10da (number of line)".

[642] Table 33: compounds of structural formulas (IB10e), (IB10ea), (IB10eb), (IB10ec), (IB10ed), (IB10ee), (IBIOef), (IB10eg) and (IB10eh), in which each groups (R ¹ ) m and (R ² ) n have the meaning defined in table 25:

N-0

(IB10e) (IB10ea) A ¹ is (= O) (IB10eb) A ¹ is (= S) (IB10ec) A ¹ is (= N-CH3) (IB10ed) A ¹ is (= N-OH) (IB10ee) A ¹ is (= N-OCH3) (IBIOef) A ¹ is (= N-NH ₂ ) (IB10eg) A ¹ is [«N-NíCH ^ J (IB10eh) A ¹ is (= N-benzyl) [643] Table 33, examples of erythro / threo mixtures (proportions from 70:30 to 30:70):

[644] Examples include the compounds of the respective structural formulas (IB10ea) to (IB10eh), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in which the meanings of groups (R ¹ ) m (R ² ) n are defined according to a line number in Table 25. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[645] Table 34: compounds of structural formulas (IB1 Of), (IBIOfa), (IB1 Ofb), (IBIOfc), (IBIOfd), (IBIOfe), (IBIOff), (IBIOfg) and (IBIOfh), where each one of

234/289 groups (R ¹ ) m and (R ² ) n have the meaning defined in table 25:

(R), (IB1 Of) (IBIOfa) A ¹ is (= O) (IBIOfb) A ¹ is (= S) (IBIOfc) A ¹ is (= N-CH3) (IBIOfd) A ¹ is (= N- OH) (IBIOfe) A ¹ is (= N-OCH3) (IB10ff) A ¹ is UN-NHJ (IB10fg) A ¹ is [= NN (CH ₃ ) 2] (IBIOfh) A ¹ is (= N-benzyl) [646] Table 34, examples of erythro / threo mixtures (proportions from 70:30 to 30:70):

[647] Examples include the compounds of the respective structural formulas (IBIOfa) to (IBIOfh), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in which the meanings of groups (R ¹ ) m (R ² ) n are defined according to a line number in Table 25. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[648] Table 35: compounds of structural formulas (IB10g), (IB10ga), (IBIOgb), (IB10gc), (IBIOgd), (IB10ge), (IBIOgf), (IBIOgg) and (IBIOgh), where each groups (R ¹ ) m and (R ² ) n have the meaning defined in table 25:

No (IB10g) (IB10ga) A ¹ is (= O) (IBIOgb) A ¹ is (= S) (IB10gc) A ¹ is (= N-CHj) (IBIOgd) A ¹ is (= N-OH) (IB10ge ) A ¹ is (= N-OCH3) (IBIOgf) A ¹ is (= N-NH2) (IBIOgg) A ¹ is [= NN (CH ₃ ) ₂ ] (IBIOgh) A ¹ is (= N-benzyl)

235/289 [649] Table 35, examples of erythro / threus mixtures (proportions from 70:30 to 30:70):

[650] Examples include the compounds of the respective structural formulas (IB10ga) to (IBIOgh), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in which the meanings of groups (R ¹ ) m (R ² ) n are defined according to a line number in Table 25. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[651] Tables 35a to 35f: compounds of structural formulas (treo-IB10ga) and (treo-2-IB10ga), in which each of the groups (R ¹ ) me (R ² ) does not have the meaning defined in table 25:

(treo-IB10ga) = (treo-1-IB10ga) + (treo-2-IB10ga) (50:50) = (rac.) [652] Table 35a (treo racemates), examples:

[653] Structural formula compounds (IB10ga) in the form of a racemic mixture of the treo [= formula (treo-IB10ga)], in which the structural combination of the groups Q, (R ¹ ) m and (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “treoIB10ga (line number)”.

[654] Table 35b (optically active treo-2 compounds), examples:

[655] Optically active treo-2 enantiomers in an enriched form [= form (2R, 3R) greater than 90% ee] which have the chemical structure of the structural formula (treo-2-IB10ga), in which the structural combination of the groups Q, (R ¹ ) m

236/289 and (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “treo-2-IB10ga (line number)”.

[656] Table 35c (optically active treo-1 enantiomers), examples:

[657] Optically active treo-1 enantiomers in an enriched form [= form (2S, 3S) greater than 90% ee] which have the chemical structure of the structural formula (treo-1-IB10ga), in which the structural combination of the groups Q, (R ¹ ) m (R ² ) n is defined according to a line number in Table 25. The individual compounds are numbered “treo-1-IB10ga (line number)”.

[658] Table 35d (racemates erythro), examples:

[659] Compounds of structural formula (IB10ga) in the form of a racemic mixture of erythro isomers [= formula (erythro-IB10ga)], where the structural combination of the groups Q, (R ¹ ) m and (R ² ) n is not defined according to a line number in Table 25. The individual compounds are numbered “eritroIB10ga (line number)”.

[660] Table 35e (erythro-1 enantiomers), examples:

[661] Optically active erythro-1 enantiomers in an enriched form [= form (2R, 3S) greater than 90% ee] which have the chemical structure of the structural formula (IB10ga) in form erythro-1 [= formula (erythro-1 -IB10ga)], where the structural combination of groups Q, (R ¹ ) m and (R ² ) n is defined according to a row number in Table 25. The individual compounds are numbered “erythro-1-IB10ga (number of line)".

[662] Table 35f (erythro-2 enantiomers) examples:

[663] Optically active erythro-2 enantiomers in an enriched form [= form (2S, 3R) greater than 90% ee] which have the chemical structure of the structural formula (IB10ga) in the form erythro-2 [= formula (erythro-2 -IB10ga)], where the structural combination of groups Q, (R ¹ ) m and (R ² ) n is defined according to a row number in Table 25. The individual compounds are numbered “erythro-2-IB10ga (number of line)".

[664] Table 36: definitions of structural combinations of groups B ² , (R ¹ ) m (R ² ) n for the following tables of the compounds of structural formula (I) of

237/289 according to the invention.

Example B ² (R ¹ ) m (R ² ) n 1 O-C (O) Et 3-F 4-Cl 2 O-C (O) Et 3-F 3-F 3 O-C (O) -i-Pr 3,4-F2 4-Cl 4 O-C (O) Me 3-F 4-Br 5 NHOH 3-Cl 3-F 6 NHOH 3,4-F2 3-F 7 NHOH H 3-F 8 NHOMe 4-F 3-F 9 NHOMe 3-F 3-Cl 10 NHOH 3,4-F2 3-Cl 11 NHNMe2 3-Br 3-F 12 O-C (O) Me 2.5-F2 3-F 13 O-C (O) Me 3-F 2-F 14 O-C (O) Me 3,4,5-Fa 4-Cl 15 OSO2Me 4-F 3-Cl 16 OSO2Me 3,4-F2 3-F, 4-Cl 17 O-C (O) Me 3,4-F2 2-F 18 O-C (O) Me 3-F 2,3-F2 19 SMe 4-F 3,5-F2 20 NHOH 3-F 4-F 21 NHOMe 3,4-F2 3-Cl, 5-F 22 OCH2OMe 3-F 3-Cl, 5-F 23 OSO2 (4-Me-Ph) 3-F 2.5-F2 24 O-C (O) Me 3,4-F2 2,3-F2 25 O-C (O) Me 3,4-F2 2.5-F2 26 SMe 3-Cl 3-Cl, 5-F 27 OSO2Me 3-F, 4-Cl 3-Cl

238/289

Example B ² (R ¹ ) m (R ² ) n 28 O-C (O) Et 3,4-F2 3-NO2 29 O-C (O) Me 3,4-F2 H 30 NHOMe 3-Cl, 4-F 3-F 31 NHOH 3,4-F2 4-OMe 32 O-C (O) -t-Bu 3-F 4-Cl 33 O-C (O) Me 3-F 4-Cl 34 OCH2OMe 3-F 4-Cl 35 SMe 3-F 4-Cl 36 OSO2 (4-Me-Ph) 3-F 4-Cl 37 Cl 3-F 4-Cl 38 OCO2Me 3-F 4-Cl 39 NHOMe 3-F 4-Cl 40 NHOH 3-F 4-Cl 41 O-C (O) -t-Bu 3-F 3-F 42 O-C (O) Me 3-F 3-F 43 OCH2Ph 3-F 3-F 44 SMe 3-F 3-F 45 OSO2 (4-Me-Ph) 3-F 3-F 46 Cl 3-F 3-F 47 OCO2Me 3-F 3-F 48 O-C (O) -t-Bu 3,4-F2 3-F 49 O-C (O) Me 3,4-F2 3-F 50 O-C (O) Et 3,4-F2 3-F 51 OSO2Me 3,4-F2 3-F 52 OCH2OMe 3,4-F2 3-F 53 OSO2 (4-Me-Ph) 3,4-F2 3-F 54 Cl 3,4-F2 3-F 55 OCO2Me 3,4-F2 3-F

239/289

Example B ² (R ¹ ) m (R ² ) n 56 NHOMe 3,4-F2 3-F 57 O-C (O) -t-Bu 3,4-F2 3-Cl 58 O-C (O) Me 3,4-F2 3-Cl 59 O-C (O) Et 3,4-F2 3-Cl 60 OCH2OMe 3,4-F2 3-Cl 61 SMe 3,4-F2 3-Cl 62 OSO2 (4-Me-Ph) 3,4-F2 3-Cl 63 Cl 3,4-F2 3-Cl 64 OCO2Me 3,4-F2 3-Cl 65 NHOMe 3,4-F2 3-Cl 66 O-C (O) -t-Bu 3-Br 3-F 67 O-C (O) Me 2.5-F2 3-F 68 SPh 3-F 2-F 69 O-C (O) -t-Bu 3,4,5-Fa 4-Cl 70 O-C (O) Me 4-F 3-Cl 71 SO2Ph 3,4-F2 3-F, 4-Cl 72 O-C (O) -t-Bu 3,4-F2 2-F 73 O-C (O) Me 3-F 2,3-F2 74 NHNH2 4-F 3,5-F2 75 O-C (O) -t-Bu 3-F 4-F 76 O-C (O) Me 3,4-F2 3-Cl, 5-F 77 NHNHMe 3-F 3-Cl, 5-F 78 O-C (O) -t-Bu 3-F 2.5-F2 79 O-C (O) Me 3,4-F2 2,3-F2 80 SPh 3,4-F2 2.5-F2 81 O-C (O) -t-Bu 3-Cl 3-Cl, 5-F 82 O-C (O) Me 3-F, 4-Cl 3-Cl 83 NHOMe 3,4-F2 3-NO2

240/289

Example B ² (R ¹ ) m (R ² ) n 84 O-C (O) -t-Bu 3,4-F2 H 85 O-C (O) Me 3-Cl, 4-F 3-F 86 SPh 3,4-F2 4-OMe 87 O-C (O) Et 3-F H 88 O-C (O) Et 3-F 2,4-F2 89 O-C (O) Et 3-F 2,6-F2 90 O-C (O) Et 3-F 3,4-F2 91 O-C (O) -i-Pr 3-F 3,5-F2 92 NHOMe 3-F 2-Cl 93 NHOH 3-F 2,3-Cb 94 NHOH 3-F 2,4-Cb 95 O-C (O) -t-Bu 3-F 2.5-Cb 96 SMe 3-F 2,6-Cb 97 NHOMe 3-F 3,4-Cb 98 O-C (O) Et 3-F 3.5-Cb 99 O-C (O) -t-Bu 3,4-F2 4-F 100 O-C (O) Me 3,4-F2 2,4-F2 101 O-C (O) -i-Pr 3,4-F2 2,6-F2 102 NHOMe 3,4-F2 3,4-F2 103 NHOH 3,4-F2 3,5-F2 104 SPh 3,4-F2 2-Cl 105 O-C (O) -t-Bu 3,4-F2 2,3-Cb 106 O-C (O) -i-Pr 3,4-F2 2,4-Cb 107 O-C (O) -t-Bu 3,4-F2 2.5-Cb 108 O-C (O) Et 3,4-F2 2,6-Cb 109 NHNH2 3,4-F2 3,4-Cb 110 NHCH2Ph 3,4-F2 3.5-Cb 111 O-C (O) -i-Pr 3-Cl H

241/289

Example B ² (R ¹ ) m (R ² ) n 112 O-C (O) -i-Pr 3-Cl 2-F 113 OSO2Me 3-Cl 4-F 114 OSO2Me 3-Cl 2,3-F2 115 O-C (O) -t-Bu 3-Cl 2,4-F2 116 NHOMe 3-Cl 2.5-F2 117 NHCH2Ph 3-Cl 2,6-F2 118 O-C (O) -t-Bu 3-Cl 3,4-F2 119 OCH2OMe 3-Cl 3,5-F2 120 OSO2Me 3-Cl 2-Cl 121 NHOMe 3-Cl 3-Cl 122 SPh 3-Cl 4-Cl 123 O-C (O) -i-Pr 3-Cl 2,3-Cb 124 O-C (O) -i-Pr 3-Cl 2,4-Cb 125 SMe 3-Cl 2.5-Cb 126 OSO2Ph 3-Cl 2,6-Cb 127 SPh 3-Cl 3,4-Cb 128 OCH2OMe 3-Cl 3.5-Cb 129 O-C (O) -i-Pr 3,4-Cb H 130 O-C (O) Me 3,4-Cb 2-F 131 O-C (O) Me 3,4-Cb 3-F 132 O-C (O) Et 3,4-Cb 4-F 133 O-C (O) Me 3,4-Cb 2,3-F2 134 O-C (O) Et 3,4-Cb 2,4-F2 135 O-C (O) Et 3,4-Cb 2.5-F2 136 O-C (O) Me 3,4-Cb 2,6-F2 137 NHOMe 3,4-Cb 3,4-F2 138 O-C (O) Et 3,4-Cb 3,5-F2 139 O-C (O) -i-Pr 3,4-Cb 2-Cl

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Example B ² (R ¹ ) m (R ² ) n 140 O-C (O) Et 3,4-Cb 3-Cl 141 O-C (O) -t-Bu 3,4-Cb 4-Cl 142 SPh 3,4-Cb 2,3-Cb 143 O-C (O) -t-Bu 3,4-Cb 2,4-Cb 144 O-C (O) Me 3,4-Cb 2.5-Cb 145 O-C (O) Et 3,4-Cb 2,6-Cb 146 O-C (O) Me 3,4-Cb 3,4-Cb 147 O-C (O) Me 3,4-Cb 3.5-Cb 148 O-C (O) Et 3-Cl, 4-F H 149 SMe 3-Cl, 4-F 2-F 150 O-C (O) Me 3-Cl, 4-F 4-F 151 O-C (O) Et 3-Cl, 4-F 2,3-F2 152 O-C (O) -t-Bu 3-Cl, 4-F 2,4-F2 153 O-C (O) Me 3-Cl, 4-F 2.5-F2 154 OSO2Me 3-Cl, 4-F 2,6-F2 155 O-C (O) Et 3-Cl, 4-F 3,4-F2 156 OSO2 (4-Me-Ph) 3-Cl, 4-F 3,5-F2 157 O-C (O) Me 3-Cl, 4-F 2-Cl 158 OCH2OMe 3-Cl, 4-F 3-Cl 159 O-C (O) Me 3-Cl, 4-F 4-Cl 160 O-C (O) Me 3-Cl, 4-F 2,3-Cb 161 O-C (O) Et 3-Cl, 4-F 2,4-Cb 162 O-C (O) Me 3-Cl, 4-F 2.5-Cb 163 O-C (O) -i-Pr 3-Cl, 4-F 2,6-Cb 164 O-C (O) Et 3-Cl, 4-F 3,4-Cb 165 O-C (O) Me 3-Cl, 4-F 3.5-Cb 166 O-C (O) Me 3-Cl, 4-F H 167 NHOH 3-F, 4-Cl 2-F

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Example B ² (R ¹ ) m (R ² ) n 168 O-C (O) Me 3-F, 4-Cl 3-F 169 O-C (O) Me 3-F, 4-Cl 4-F 170 NHOMe 3-F, 4-Cl 2,3-F2 171 O-C (O) Et 3-F, 4-Cl 2,4-F2 172 SPh 3-F, 4-Cl 2.5-F2 173 O-C (O) Me 3-F, 4-Cl 2,6-F2 174 O-C (O) Me 3-F, 4-Cl 3,4-F2 175 O-C (O) Et 3-F, 4-Cl 3,5-F2 176 O-C (O) Me 3-F, 4-Cl 2-Cl 177 O-C (O) Et 3-F, 4-Cl 4-Cl 178 SPh 3-F, 4-Cl 2,3-Cb 179 NHOMe 3-F, 4-Cl 2,4-Cb 180 NHOMe 3-F, 4-Cl 2.5-Cb 181 O-C (O) -i-Pr 3-F, 4-Cl 2,6-Cb 182 SMe 3-F, 4-Cl 3,4-Cb 183 SPh 3-F, 4-Cl 3.5-Cb 184 O-C (O) Et 3-F 2.5-F2 185 O-C (O) Me 3-F 2,6-F2 186 SPh 3-F 2,6-F2 187 NHNH2 3,4-F2 3,4-Cb 188 NHCH2Ph 3,4-F2 3.5-Cb 189 SPh 3-F 2,6-F2 190 O-C (O) -t-Bu 3-F 2,6-F2 191 SMe 3-F 2,6-F2 192 O-C (O) Et 3,4-F2 2,6-F2 193 O-C (O) -t-Bu 3,4-F2 2,6-F2 194 O-C (O) Me 3,4-F2 2,6-F2 195 SPh 3,4-F2 2,6-F2

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Example B ² (R ¹ ) m (R ² ) n 196 SMe 3,4-F2 2,6-F2 197 OSO2 (4-Me-Ph) 3,4-F2 2,6-F2 198 Cl 3,4-F2 2,6-F2 199 OCO2Me 3,4-F2 2,6-F2 200 OCH2OMe 3,4-F2 2,6-F2 201 O-C (O) Et H 2,6-F2 202 O-C (O) Et H 3,4-F2 203 O-C (O) Me H 3,5-F2 204 NHOMe H 2-Cl 205 NHOH H 3-Cl 206 O-C (O) Et H 4-Cl 207 SMe H 2,3-Cb 208 SPh H 2,4-Cb 209 NHCH2Ph H 2.5-Cb 210 O-C (O) Et H 2,6-Cb 211 OCH2OMe H 3,4-Cb 212 OCH2OMe H 3.5-Cb 213 O-C (O) Et 3-CN 2.5-F2 214 O-C (O) -t-Bu 3-CN 2.5-F2 215 O-C (O) Me 3-CN 2.5-F2 216 NHOMe 3-CN 2.5-F2 217 SMe 3-CN 2.5-F2 218 OSO2 (4-Me-Ph) 3-CN 2.5-F2 219 Cl 3-CN 2.5-F2 220 OCO2Me 3-CN 2.5-F2 221 O-C (O) Et 3-CN 2,6-F2 222 NHOMe 3-CN 2,6-F2 223 O-C (O) Me 3-CN 2,6-F2

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Example B ² (R ¹ ) m (R ² ) n 224 NHOH 3-CN 2,6-F2 225 SMe 3-CN 2,6-F2 226 OSO2 (4-Me-Ph) 3-CN 2,6-F2 227 Cl 3-CN 2,6-F2 228 OCO2Me 3-CN 2,6-F2 229 O-C (O) Et 3-CN 2,3-F2 230 O-C (O) -t-Bu 3-CN 2,3-F2 231 O-C (O) Me 3-CN 2,3-F2 232 SPh 3-CN 2,3-F2 233 SMe 3-CN 2,3-F2 234 NHOH 3-CN 2,3-F2 235 Cl 3-CN 2,3-F2 236 OCO2Me 3-CN 2,3-F2 237 O-C (O) Et 3-CN 2,4-F2 238 NHNH2 3-CN 2,4-F2 239 O-C (O) Me 3-CN 2,4-F2 240 NHNH2 3-CN 2,4-F2 241 SMe 3-CN 2,4-F2 242 OSO2 (4-Me-Ph) 3-CN 2,4-F2 243 Cl 3-CN 2,4-F2 244 OCO2Me 3-CN 2,4-F2 245 O-C (O) Et 3-CN 2,4-F2 246 O-C (O) -t-Bu 3-CN 2,4-F2 247 O-C (O) Me 3-CN 2,4-F2 248 SPh 3-CN 2,4-F2 249 SMe 3-CN 2,4-F2 250 OSO2 (4-Me-Ph) 3-CN 2,4-F2 251 Cl 3-CN 2,4-F2

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Example B ² (R ¹ ) m (R ² ) n 252 OCO2Me 3-CN 2,4-F2 253 O-C (O) Et 3-CN 4-Cl 254 NHOMe 3-CN 4-Cl 255 O-C (O) Me 3-CN 4-Cl 256 NHOMe 3-CN 4-Cl 257 SMe 3-CN 4-Cl 258 OSO2 (4-Me-Ph) 3-CN 4-Cl 259 Cl 3-CN 4-Cl 260 OCO2Me 3-CN 4-Cl 261 O-C (O) Et 3-CN 3-Cl 262 NHOMe 3-CN 3-Cl 263 O-C (O) Me 3-CN 3-Cl 264 NHOH 3-CN 3-Cl 265 SMe 3-CN 3-Cl 266 OSO2 (4-Me-Ph) 3-CN 3-Cl 267 Cl 3-CN 3-Cl 268 OCO2Me 3-CN 3-Cl 269 O-C (O) Et 3-CN 4-F 270 NHOMe 3-CN 4-F 271 O-C (O) Me 3-CN 4-F 272 NHOMe 3-CN 4-F 273 SMe 3-CN 4-F 274 OSO2 (4-Me-Ph) 3-CN 4-F 275 Cl 3-CN 4-F 276 OCO2Me 3-CN 4-F 277 O-C (O) Et 3-CN 3-F 278 NHOMe 3-CN 3-F 279 O-C (O) Me 3-CN 3-F

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Example B ² (R ¹ ) m (R ² ) n 280 NHOH 3-CN 3-F 281 SMe 3-CN 3-F 282 OSO2 (4-Me-Ph) 3-CN 3-F 283 Cl 3-CN 3-F 284 OCO2Me 3-CN 3-F 285 O-C (O) Et 3-NO2 2.5-F2 286 NHCH2Ph 3-NO2 2.5-F2 287 O-C (O) Me 3-NO2 2.5-F2 288 NHOMe 3-NO2 2.5-F2 289 SMe 3-NO2 2.5-F2 290 OSO2 (4-Me-Ph) 3-NO2 2.5-F2 291 Cl 3-NO2 2.5-F2 292 OCO2Me 3-NO2 2.5-F2 293 O-C (O) Et 3-NO2 2,6-F2 294 O-C (O) -t-Bu 3-NO2 2,6-F2 295 O-C (O) Me 3-NO2 2,6-F2 296 NHOMe 3-NO2 2,6-F2 297 SMe 3-NO2 2,6-F2 298 NHOH 3-NO2 2,6-F2 299 Cl 3-NO2 2,6-F2 300 OCO2Me 3-NO2 2,6-F2 301 O-C (O) Et 3-NO2 2,3-F2 302 O-C (O) -t-Bu 3-NO2 2,3-F2 303 O-C (O) Me 3-NO2 2,3-F2 304 SPh 3-NO2 2,3-F2 305 SMe 3-NO2 2,3-F2 306 OSO2 (4-Me-Ph) 3-NO2 2,3-F2 307 Cl 3-NO2 2,3-F2

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Example B ² (R ¹ ) m (R ² ) n 308 OCO2Me 3-NO2 2,3-F2 309 O-C (O) Et 3-NO2 2,4-F2 310 O-C (O) -t-Bu 3-NO2 2,4-F2 311 O-C (O) Me 3-NO2 2,4-F2 312 NHOMe 3-NO2 2,4-F2 313 SMe 3-NO2 2,4-F2 314 OSO2 (4-Me-Ph) 3-NO2 2,4-F2 315 Cl 3-NO2 2,4-F2 316 OCO2Me 3-NO2 2,4-F2 317 O-C (O) Et 3-NO2 2,4-F2 318 O-C (O) -t-Bu 3-NO2 2,4-F2 319 O-C (O) Me 3-NO2 2,4-F2 320 SPh 3-NO2 2,4-F2 321 SMe 3-NO2 2,4-F2 322 OSO2 (4-Me-Ph) 3-NO2 2,4-F2 323 Cl 3-NO2 2,4-F2 324 OCO2Me 3-NO2 2,4-F2 325 O-C (O) Et 3-NO2 4-Cl 326 NHOMe 3-NO2 4-Cl 327 O-C (O) Me 3-NO2 4-Cl 328 SPh 3-NO2 4-Cl 329 SMe 3-NO2 4-Cl 330 NHOH 3-NO2 4-Cl 331 Cl 3-NO2 4-Cl 332 OCO2Me 3-NO2 4-Cl 333 O-C (O) Et 3-NO2 3-Cl 334 O-C (O) -t-Bu 3-NO2 3-Cl 335 O-C (O) Me 3-NO2 3-Cl

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Example B ² (R ¹ ) m (R ² ) n 336 SPh 3-NO2 3-Cl 337 SMe 3-NO2 3-Cl 338 NHOMe 3-NO2 3-Cl 339 Cl 3-NO2 3-Cl 340 OCO2Me 3-NO2 3-Cl 341 O-C (O) Et 3-NO2 4-F 342 O-C (O) -t-Bu 3-NO2 4-F 343 O-C (O) Me 3-NO2 4-F 344 SPh 3-NO2 4-F 345 SMe 3-NO2 4-F 346 NHOMe 3-NO2 4-F 347 Cl 3-NO2 4-F 348 OCO2Me 3-NO2 4-F 349 O-C (O) Et 3-NO2 3-F 350 NHOMe 3-NO2 3-F 351 O-C (O) Me 3-NO2 3-F 352 SPh 3-NO2 3-F 353 SMe 3-NO2 3-F 354 NHOH 3-NO2 3-F 355 Cl 3-NO2 3-F 356 OCO2Me 3-NO2 3-F 357 O-C (O) Et 3-CN, 4-F 2,6-F2 358 NHOMe 3-CN, 4-F 2,6-F2 359 O-C (O) Me 3-CN, 4-F 2,6-F2 360 SPh 3-CN, 4-F 2,6-F2 361 SMe 3-CN, 4-F 2,6-F2 362 NHOH 3-CN, 4-F 2,6-F2 363 Cl 3-CN, 4-F 2,6-F2

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Example B ² (R ¹ ) m (R ² ) n 364 OCO2Me 3-CN, 4-F 2,6-F2 365 O-C (O) Me 3-CN, 4-F 3-Cl 366 O-C (O) Me 3-CN, 4-F 3-CN 367 O-C (O) Me 3-CN, 4-F 4-F 368 O-C (O) Me 3-CN, 4-F 4-Cl 369 O-C (O) Me 3-CN, 4-F 2.5-F2 370 O-C (O) Me 3-CN, 4-F 2,6-F2 371 O-C (O) Et 3-Br, 4-F 2,6-F2 372 NHOMe 3-Br, 4-F 2,6-F2 373 O-C (O) Me 3-Br, 4-F 2,6-F2 374 SPh 3-Br, 4-F 2,6-F2 375 SMe 3-Br, 4-F 2,6-F2 376 NHOH 3-Br, 4-F 2,6-F2 377 Cl 3-Br, 4-F 2,6-F2 378 OCO2Me 3-Br, 4-F 2,6-F2 379 O-C (O) Me 3-Br, 4-F 3-Cl 380 O-C (O) Me 3-Br, 4-F 3-CN 381 O-C (O) Me 3-Br, 4-F 4-F 382 O-C (O) Me 3-Br, 4-F 4-Cl 383 O-C (O) Me 3-Br, 4-F 2.5-F2 384 O-C (O) Me 3-Br, 4-F 2,6-F2 385 O-C (O) Et 3-F, 4-CN 3-F 386 NHOMe 3-F, 4-CN 3-Cl 387 O-C (O) Me 3-F, 4-CN 3-CN 388 SPh 3-F, 4-CN 4-F 389 SMe 3-F, 4-CN 4-Cl 390 NHOH 3-F, 4-CN 2.5-F2 391 Cl 3-F, 4-CN 2,6-F2

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Example B ² (R ¹ ) m (R ² ) n 392 OCO2Me 3-F, 4-CN 3-F 393 O-C (O) Me 3-F, 4-CN 3-Cl 394 O-C (O) Me 3-F, 4-CN 3-CN 395 O-C (O) Me 3-F, 4-CN 4-F 396 O-C (O) Me 3-F, 4-CN 4-Cl 397 O-C (O) Me 3-F, 4-CN 2.5-F2 398 O-C (O) Me 3-F, 4-CN 2,6-F2

[665] For reference purposes, specific numbers (= example numbers) have been assigned to individual compounds in Tables 37 to 42 below, where the example number in question consists of the number of the chemical formula assigned to the respective table and a “number line ”(line number) which refers to the same number in the row in the first column of table 36. The chemical structure of example no. “(Formula number) (line number)” is thus unambiguously defined by the previous formula in the respective table by the formula number and line number in table 36, for example:

[666] Example no. “IA5a1” in Table 37 is the compound of structural formula (IA5a), where B ² = -OC (O) -Et, (R ¹ ) m = 3-F and (R ² ) n = 4-Cl, defined according to row 1 of table 36, or a tautomer thereof;

[667] example no. “IA12ab344” in Table 38 is the compound of structural formula (IA12a), where R = ethyl [= sub-formula (IA12ab)], where B ² = phenylthio, (R ¹ ) m = 3-NO2 and (R ² ) n = 4-F, defined according to line 344 of table 36, or a tautomer thereof.

[668] Table 37: compounds of structural formula (IA5a), in which groups B ² , (R ¹ ) m and (R ² ) do not have the meanings defined in table 36:

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CH '3

X

(IA5a) [669] Table 37, examples:

[670] Examples include the compounds of structural formula (IA5a), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in which the meanings of groups B ² , (R ¹ ) m (R ² ) n are defined according to a line number in Table 36, The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[671] Table 38: compounds of structural formulas (IA12a), (IA12aa), (IA12ab), (IA12ac) and (IA12ad), in which groups B ² , (R ¹ ) m and (R ² ) do not have the meanings defined in table 36:

R o o

(IA12a) (IA12aa) R is methyl (IA12ab) R is ethyl (IA12ac) R is n-propyl (IA12ad) R is i-propllo [672] Table 38, examples of erythro / threus mixtures (proportions from 70:30 to 30 : 70):

[673] Examples include the compounds of structural formulas (IA12aa) 15 a (IA12ad), in each case in the form of an erythro / racemic mixture (ratio 70:30 to 30:70), in which the meanings of groups B ² , (R ¹ ) m (R ² ) _n are defined according to a line number in Table 36. The individual compounds are numbered “(formula) (line number)”, without

253/289 any parentheses.

[674] Tables 38a to 38f: compounds of structural formulas (treo-IA12aa), (treo-IA12ab), (treo-IA12ac), (treo-IA12ad), (treo-2-IA12aa), (treo-2-IA12ab ), (treo-2-IA12ac) and (treo-2-IA12ad), in which each of the groups B ² , (R ¹ ) m and (R ² ) does not have the meaning defined in table 36:

(treo-1-IA12aa) R = OCH ₃ (treo-1-IA12ab) R = OC ₂ H ₅ (treo-1 -IA12ac) R = nC ₃ H ₇ (treo-1 -1A12ad) R = iC ₃ H ₇

(treo-2-IA12aa) R = OCH ₃ (treo-2-IA12ab) R = OC ₂ H ₅ (treo-2-IA12ac) R = nC ₃ H ₇ (treo-2-IA12ad) R = iC ₃ H ₇ (treo-lA12aa) = (treo-1-IA12aa) + (treo-2-IA12aa) (50:50) = (rac.) (treo-IA12ab) = (treo-1-IA12ab) + (treo-2- IA12ab) (50:50) = (rac.) (Treo-LA12ac) = (treal-IA12ac) + (treo-2-IA12ac) (50:50) = (rac.) (Treo-IA12ad) = (treo- 1-IA12ad) + (treo-2-LA12ad) (50:50) = (rac.) [675] Table 38a (treo racemates), examples:

[676] Compounds of structural formulas treo- (IA12aa), treo- (IA12ab), treo (IA12ac) and treo- (IA12ad), in each case in the form of racemic mixture of the treo isomers, in which the structural combination of the groups B ² , (R ¹ ) m (R ² ) n is defined according to a line number in Table 36. The individual compounds are numbered “treo-IA12aa (line number)”, “treo-IA12ab (line number ) ”,“ Treo-IA12ac (line number) ”and“ treo-IA12ad (line number) ”.

[677] Table 38b, examples (optically active treo-2 enantiomers):

[678] Optically active treo-2 enantiomers in an enriched form [= form (2R, 3R) greater than 90% ee] which have the chemical structure of the structural formula treo-2- (IA12aa), treo-2- (IA12ab) , treo-2- (IA12ac) or treo-2- (IA12ad),

254/289 where the structural combination of groups B ² , (R ¹ ) m and (R ² ) n is defined according to a row number in Table 36. The individual compounds are numbered “treo-2-IA12aa (number of line) "," treo-2-IA12ab (line number) "," treo-2IA12ac (line number) "and" treo-2-IA12ad (line number) ".

[679] Table 38c, examples (optically active treo-1 enantiomers):

[680] Optically active treo-1 enantiomers in an enriched form [= form (2S, 3S) greater than 90% ee] which have the chemical structure of the structural formula treo-1- (IA12aa), treo-1- (IA12ab) , treo-1- (IA12ac) or treo-1- (IA12ad), where the structural combination of groups B ² , (R ¹ ) m and (R ² ) n is defined according to a line number in table 36. The individual compounds are numbered "treo-1-IA12aa (line number)", "treo-1-IA12ab (line number)", "treo-1IA12ac (line number)" and "treo-1-IA12ad (number of line)".

[681] Table 38d (erythro racemates), examples:

[682] Compounds of structural formulas erythro- (IA12aa), erythro- (IA12ab), erythro (IA12ac) and erythro- (IA12ad), in each case in the form of a racemic mixture of erythro isomers, in which the structural combination of groups B ² , (R ¹ ) m (R ² ) n is defined according to a line number in table 36. The individual compounds are numbered “erythro-IA12aa (line number)”, “erythroIA12ab (line number) ”,“ Eritro-IA12ac (line number) ”and“ eritroIA12ad (line number) ”.

[683] Table 38e (erythro-1 enantiomers), examples:

[684] Optically active erythro-2 enantiomers in an enriched form [= form (2R, 3S) greater than 90% ee] which have the chemical structure of the structural formula erythro-1- (IA12aa), erythro-1- (IA12ab) , erythro-1- (IA12ac) or erythro1- (IA12ad), where the structural combination of groups B ² , (R ¹ ) m and (R ² ) n is defined according to a line number in Table 36. The compounds individual numbers are numbered “erythro-1-IA12aa (line number)”, “erythro-1IA12ab (line number)”, “erythro-1-IA12ac (line number)” and “eritro-1IA12ad (line number)” .

[685] Table 38f (erythro-2 enantiomers) examples:

255/289 [686] Optically active erythro-2 enantiomers in an enriched form [= form (2S, 3R) greater than 90% ee] which have the chemical structure of the structural formula erythro-2- (IA12aa), erythro-2- (IA12ab), erythro-2- (IA12ac) or erythro2- (IA12ad), where the structural combination of groups B ² , (R ¹ ) m and (R ² ) n is defined according to a line number in Table 36 The individual compounds are numbered “erythro-2-IA12aa (line number)”, “erythro-2IA12ab (line number)”, “erythro-2-IA12ac (line number)” and “erythro-2IA12ad (number of line)".

[687] Table 39: compounds of structural formulas (IA10a), (IA10aa), (IA10ab), (IA10ac) and (IA10ad), in which groups B ² , (R ¹ ) m and (R ² ) do not have the meanings defined in table 36:

R

(IA10a) (IA10aa) R is methyl (IA10ab) R is ethyl (lA10ac) R is n-propyl (IA10ad) R is i-propyl [688] Table 39, examples of erythro / threus mixtures (proportions from 70:30 to 30:70):

[689] Examples include compounds of structural formulas (IA10aa) to (IA10ad), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in which the meanings of groups B ² , (R ¹ ) m (R ² ) _n are defined according to a line number in Table 36. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[690] Tables 39a to 39f: compounds of structural formulas (treo-IA10aa), (treo-IA10ab), (treo-IA10ac), (treo-IA10ad), (treo-2-IA10aa), (treo-2-IA10ab ), (treo-2-IA10ac) and (treo-2-IA10ad), in which each of the groups B ² , (R ¹ ) m and (R ² ) does not have the meaning defined in table 36:

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R

R

Ç ^H 3 O

(treo-1-IA1 Oaa) R = OCH ₃ (treo-1-IA1 Oab) R = OC ₂ K ₅ (treo-1-IA1 Oac) R = nC ₃ H ₇ (treo-1-IA1 Oad) R = iC ₃ H ₇ (treo-2-IA1 Oaa) R = OCH ₃ (treo-2-IA10ab) R = OC ₂ H ₅ (treo-2-IA1 Oac) R = nC ₃ H ₇ (trec-2-IA10ad) R = iC ₃ H ₇ (treo-IA1 Oaa) = (treo-1 -IA1 Oaa) + (treo-2-IA1 Oaa) (50:50) = (rac.) (Treo-IA10ab) = (treo-1 -IA1 Oab) + (treo-2-IA1 Oab) (50:50) = (rac.) (Treo-IA10ac) = (treo-1-IA1 Oac) + (treo-2-IA1 Oac) (50:50 ) = (rac.) (treo-IA10ad) = (treo-1-IA1 Oad) + (treo-2-1 A1 Oad) (50:50) = (rac.) [691] Table 39a (treo racemates), examples:

[692] Compounds of structural formulas treo- (IAIOaa), treo- (IAIOab), treo5 (IA10ac) and treo- (IAIOad), in each case in the form of a racemic mixture of the treo isomers, in which the structural combination of the groups B ² , (R ¹ ) m (R ² ) n is defined according to a line number in Table 36. The individual compounds are numbered “treo-IA10aa (line number)”, “treo-IA10ab (line number ) ”,“ Treo-IA10ac (line number) ”and“ treo-IA10ad (line number) ”.

[693] Table 39b (optically active treo-2 enantiomers), examples:

[694] Optically active treo-2 enantiomers in an enriched form [= form (2R, 3R) greater than 90% ee] which have the chemical structure of the structural formula treo-2- (IA10aa), treo-2- (IA10ab) , treo-2- (IA10ac) or treo-2- (IA10ad), where the structural combination of groups B ² , (R ¹ ) m and (R ² ) n is defined according to a line number in table 36. The individual compounds are numbered "treo-2-IA10aa (line number)", "treo-2-IA10ab (line number)", "treo-2 IA10ac (line number)" and "treo-2-IA10ad ( line number) ”.

257/289 [695] Table 39c, examples (optically active treo-1 enantiomers):

[696] Treo-1 optically active enantiomers in an enriched form [= form (2S, 3S) greater than 90% ee] which have the chemical structure of the structural formula treo-1- (IA10aa), treo-1- (IA10ab) , treo-1- (IA10ac) or treo-1- (IA10ad), where the structural combination of groups B ² , (R ¹ ) m and (R ² ) n is defined according to a line number in table 36. The individual compounds are numbered “treo-1-IA10aa (line number)”, “treo-1-IA10ab (line number)”, “treo-1IA10ac (line number)” and “treo-1-IA10ad (number of line)".

[697] Table 39d (erythro racemates), examples:

[698] Compounds of structural formulas erythro- (IA10aa), erythro- (IA10ab), erythro (IA10ac) and erythro- (IA10ad), in each case in the form of a racemic mixture of erythro isomers, in which the structural combination of groups B ² , (R ¹ ) m (R ² ) n is defined according to a line number in Table 36. The individual compounds are numbered “erythro-IA10aa (line number)”, “erythroIA10ab (line number) ”,“ Eritro-IA10ac (line number) ”and“ eritroIA10ad (line number) ”.

[699] Table 39e (erythro-1 enantiomers), examples:

[700] Optically active erythro-2 enantiomers in an enriched form [= form (2R, 3S) greater than 90% ee] which have the chemical structure of the structural formula erythro-1- (IA10aa), erythro-1- (IA10ab) , erythro-1- (IA10ac) or erythro1- (IA10ad), where the structural combination of groups B ² , (R ¹ ) m and (R ² ) n is defined according to a line number in Table 36. The compounds individual numbers are numbered “erythro-1-IA10aa (line number)”, “erythro-1IA10ab (line number)”, “erythro-1-IA10ac (line number)” and “eritro-1IA10ad (line number)” .

[701] Table 39f (erythro-2 enantiomers) examples:

[702] Optically active erythro-2 enantiomers in an enriched form [= form (2S, 3R) greater than 90% ee] which have the chemical structure of the structural formula erythro-2- (IA10aa), erythro-2- (IA10ab) , erythro-2- (IA10ac) or erythro2- (IA10ad), where the structural combination of groups B ² , (R ¹ ) m and (R ² ) n is

258/289 defined according to a line number in Table 36. The individual compounds are numbered “erythro-2-IA10aa (line number)”, “erythro-2IA10ab (line number)”, “eritro-2-IA10ac (line number) ”and“ eritro-2IA10ad (line number) ”.

[703] Table 40: compounds of structural formulas (IA10b), (IA10ba), (IA10bb), (IA10bc) and (IA10bd), in which groups B ² , (R ¹ ) m and (R ² ) do not have the meanings defined in table 36:

R

O

(IA10b) (IA10ba) R is methyl (IA10bb) R is ethyl (IA10bc) R is-propyl (IA10bd) R is-propyl [704] Table 40, examples of erythro / threus mixtures (proportions from 70:30 to

30:70):

[705] Examples include compounds of structural formulas (IA10ba) to (IA10bd), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in which the meanings of groups B ² , (R ¹ ) m (R ² ) _n are defined according to a line number in Table 36. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[706] Tables 40a to 40f: compounds of structural formulas (treo-IA10ba), (treo-IA10bb), (treo-IA10bc), (treo-IA10bd), (treo-2-IA10ba), (treo-2-IA10bb ), (treo-2-IA10bc) and (treo-2-IA10bd), in which each of the groups B ² , (R ¹ ) m and (R ² ) does not have the meaning defined in table 36:

259/289

R

R

O

(treo-1-IA1 Oba) R = OCH ₃ (treo-1-IA1 Obb) R = OC ₂ H ₅ (treo-1-IA1 Obc) R = nC ₃ H ₇ (trec-1-IA10bd) R = iC ₃ H ₇ (treo-2-1 A1 Oba) R = OCH (treo-2-1 A1 Obb) R = OC ₂ H ₅ (treo-2-IA1 Obc) R = nC ₃ H ₇ (trec-2-IA10bd ) R = iC ₃ H ₇ '3 (treo-l A1 Oba) = (treo-1-1A1 Oba) + (treo-2-IA1 Oba) (50:50) = (rac.) (Treo- | A1 Obb ) = (treo-1-IA1 Obb) + (treo-2-IA1 Obb) (50:50) = (rac.) (treo-IA10bc) = (treo-1-IA1 Obc) + (treo-2-IA1 Obc) (50:50) = (rac.) (Treo-IA10bd) = (treo-1-IA10 bd) + (treo-2-la1 Obd) (50:50) = (rac.) [707] Table 40a (treo racemates), examples:

[708] Compounds of structural formulas treo- (IAIOba), treo- (IAIObb), treo (IA10bc) and treo- (IAIObd), in each case in the form of racemic mixture of the treo isomers, in which the structural combination of the groups B ² , (R ¹ ) m (R ² ) n is defined according to a line number in Table 36. The individual compounds are numbered “treo-IA10ba (line number)”, “treo-IA10bb (line number ) ”,“ Treo-IA10bc (line number) ”and“ treo-IA10bd (line number) ”.

[709] Table 40b (optically active treo-2 enantiomers), examples:

[710] Optically active treo-2 enantiomers in an enriched form [= form (2R, 3R) greater than 90% ee] which have the chemical structure of the structural formula treo-2- (IA10ba), treo-2- (IA10bb) , treo-2- (IA10bc) or treo-2- (IA10bd), where the structural combination of groups B ² , (R ¹ ) m and (R ² ) n is defined according to a line number in table 36. The individual compounds are numbered "treo-2-IA10ba (line number)", "treo-2-IA10bb (line number)", "treo-2 IA10bc (line number)" and "treo-2-IA10bd ( line number) ”.

[711] Table 40c, examples (optically active treo-1 enantiomers):

260/289 [712] Optically active treo-1 enantiomers in an enriched form [= form (2S, 3S) greater than 90% ee] which have the chemical structure of the structural formula treo-1 - (IA10ba), treo-1- (IA10bb), treo-1- (IA10bc) or treo-1- (IA10bd), where the structural combination of groups B ² , (R ¹ ) m and (R ² ) n is defined according to a line number of the table 36. The individual compounds are numbered “treo-1-IA10ba (line number)”, “treo-1-IA10bb (line number)”, “treo-1IA10bc (line number)” and “treo-1- IA10bd (line number) ”.

[713] Table 40d (racemates erythro), examples:

[714] Compounds of structural formulas erythro- (IA10ba), erythro- (IA10bb), erythro (IA10bc) and erythro- (IA10bd), in each case in the form of a racemic mixture of erythro isomers, in which the structural combination of groups B ² , (R ¹ ) m (R ² ) n is defined according to a line number in Table 36. The individual compounds are numbered “erythro-IA10ba (line number)”, “erythroIA10bb (line number) ”,“ Eritro-IA10bc (line number) ”and“ eritroIA10bd (line number) ”.

[715] Table 40e (erythro-1 enantiomers), examples:

[716] Optically active erythro-2 enantiomers in an enriched form [= form (2R, 3S) greater than 90% ee] which have the chemical structure of the structural formula erythro-1- (IA10ba), erythro-1- (IA10bb) , erythro-1- (IA10bc) or erythro1- (IA10bd), where the structural combination of groups B ² , (R ¹ ) m and (R ² ) n is defined according to a line number in Table 36. The compounds individual numbers are numbered “erythro-1-IA10ba (line number)”, “erythro-1IA10bb (line number)”, “erythro-1-IA10bc (line number)” and “eritro-1IA10bd (line number)” .

[717] Table 40f (erythro-2 enantiomers) examples:

[718] Optically active erythro-2 enantiomers in an enriched form [= form (2S, 3R) greater than 90% ee] which have the chemical structure of the structural formula erythro-2- (IA10ba), erythro-2- (IA10bb) , erythro-2- (IA10bc) or erythro2- (IA10bd), where the structural combination of groups B ² , (R ¹ ) m and (R ² ) n is defined according to a line number in Table 36. The compounds

261/289 individual numbers are numbered “erythro-2-IA10ba (line number)”, “erythro-2IA10bb (line number)”, “erythro-2-IA10bc (line number)” and “eritro-2IA10bd (number of line)".

[719] Table 41: compounds of structural formulas (IA11a), (IA11aa), (IA11ab), (IA11ac) and (IA11ad), in which groups B ² , (R ¹ ) m and (R ² ) do not have the meanings defined in table 36:

(IA11a) (IA11aa) R ethyl (IA11ab) R ethyl (IA11ac) R et-propyl (IA11ad) R et-propyl [720] Table 41, examples of erythro / threus mixtures (proportions from 70:30 to 30:70) :

[721] Examples include compounds of structural formulas (IA11aa) to (IA11ad), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in which the meanings of groups B ² , (R ¹ ) m (R ² ) _n are defined according to a line number in Table 36. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[722] Tables 41a to 41f: compounds of structural formulas (treo-IA11aa), (treo-IA11ab), (treo-IA11ac), (treo-IA11ad), (treo-2-IA11aa), (treo-2-IA11ab ), (treo-2-IA11ac) and (treo-2-IA11ad), in which each of the groups B ² , (R ¹ ) me (R ² ) n

262/289

R

R

The CH

(treo-1-IA11aa) R = OCH ₃ (treo-1-IA11ab) R = OC ₂ H ₅ (treo-1-IA11 ac) R = nC ₃ H ₇ (trec-1-IA11ad) R = iC ₃ H ₇ (treo-2-IA11aa) R = OCH ₃ (treo-2-IA11ab) R = OC ₂ H ₅ (treo-2-IA11ac) R = nC ₃ H ₇ (trec-2-LA11 ad) R = iC ₃ H ₇ (treo-IA11aa) = (treo-1-IA11 aa) + (treo-2-IA11aa) (50:50) = (rac.) (Treo-lA11ab) = (treo-1-IA11 ab) + ( treo-2-IA11 ab) (50:50) = (rac.) (treo-LA11 ac) = (treo-1-IA11 ac) + (treo-2-IA11 ac) (50:50) = (rac. ) (treo-IA11ad) = (treo-1-IA11 ad) + (treo-2-IA11 ad) (50:50) = (rac.) [723] Table 41a (treo racemates), examples:

[724] Compounds of structural formulas treo- (IA11aa), treo- (IA11ab), treo (IA11ac) and treo- (IA11ad), in each case in the form of a racemic mixture of the treo isomers, in which the structural combination of the groups B ² , (R ¹ ) m (R ² ) n is defined according to a line number in Table 36. The individual compounds are numbered “treo-IA11aa (line number)”, “treo-IA11ab (line number ) ”,“ Treo-IA11ac (line number) ”and“ treo-IA11ad (line number) ”.

[725] Table 41b (optically active treo-2 enantiomers), examples:

[726] Optically active treo-2 enantiomers in an enriched form [= form (2R, 3R) greater than 90% ee] which have the chemical structure of the structural formula treo-2- (IA11aa), treo-2- (IA11ab) , treo-2- (IA11ac) or treo-2- (IA11ad), where the structural combination of groups B ² , (R ¹ ) m and (R ² ) n is defined according to a line number in table 36. The individual compounds are numbered "treo-2-IA11aa (line number)", "treo-2-IA11ab (line number)", "treo-2 IA11ac (line number)" and "treo-2-IA11ad ( line number) ”.

[727] Table 41c, examples (optically active treo-1 enantiomers):

263/289 [728] Optically active treo-1 enantiomers in an enriched form [= form (2S, 3S) greater than 90% ee] which have the chemical structure of the structural formula treo-1- (IA11aa), treo-1- (IA11ab), treo-1- (IA11ac) or treo-1- (IA11ad), in which the structural combination of groups B ² , (R ¹ ) m and (R ² ) n is defined according to a line number of the table 36. The individual compounds are numbered “treo-1-IA11aa (line number)”, “treo-1-IA11ab (line number)”, “treo-1IA11ac (line number)” and “treo-1- IA11ad (line number) ”.

[729] Table 41d (erythro racemates), examples:

[730] Compounds of structural formulas erythro- (IA11aa), erythro- (IA11ab), erythro (IA11ac) and erythro- (IA11ad), in each case in the form of a racemic mixture of erythro isomers, in which the structural combination of groups B ² , (R ¹ ) m and (R ² ) n are defined according to a line number in Table 36. The individual compounds are numbered “erythro-IA11aa (line number)”, “erythroIA11ab (line number) ”,“ Eritro-IA11ac (line number) ”and“ eritroIA11ad (line number) ”.

[731] Table 41e (erythro-1 enantiomers), examples:

[732] Optically active erythro-2 enantiomers in an enriched form [= form (2R, 3S) greater than 90% ee] which have the chemical structure of the structural formula erythro-1- (IA11aa), erythro-1- (IA11ab) , erythro-1- (IA11ac) or erythro1- (IA11ad), where the structural combination of groups B ² , (R ¹ ) m and (R ² ) n is defined according to a line number in Table 36. The compounds individual numbers are numbered “eritro-1-IA11aa (line number)”, eritro-1IA11ab (line number) ”,“ eritro-1-IA11ac (line number) ”and“ eritro-1IA11ad (line number) ”.

[733] Table 41f (erythro-2 enantiomers) examples:

[734] Optically active erythro-2 enantiomers in an enriched form [= form (2S, 3R) greater than 90% ee] which have the chemical structure of the structural formula erythro-2- (IA11aa), erythro-2- (IA11ab) , erythro-2- (IA11ac) or erythro2- (IA11ad), where the structural combination of groups B ² , (R ¹ ) m and (R ² ) n is defined according to a line number in Table 36. The compounds

264/289 individual numbers are numbered “eritro-2-IA11aa (line number)”, “eritro-2IA11ab (line number)”, “eritro-2-IA11ac (line number)” and “eritro-2IA11ad (number of line)".

[735] Table 42: compounds of structural formulas (IA11b), (IA11ba), (IA11 bb), (IA11bc) and (IA11 bd), in which groups B ² , (R ¹ ) m and (R ² ) do not have the meanings defined in table 35:

(IA11b) (IA11ba) R is methyl (IA11bb) R ethyl (IA11bc) R is propyl (IA11bd) R is i-propyl [736] Table 42, examples of erythro / threus mixtures (proportions from 70:30 to

30:70):

[737] Examples include the compounds of structural formulas (IA11ba) to (IA11bd), in each case in the form of an erythro / racemic mixture (ratio from 70:30 to 30:70), in which the meanings of groups B ² , (R ¹ ) m (R ² ) _n are defined according to a line number in Table 36. The individual compounds are numbered “(formula) (line number)”, without any parentheses.

[738] Tables 42a to 42f: compounds of structural formulas (treo-IA11ba), (treo-IA11bb), (treo-IA11bc), (treo-IA11bd), (treo-2-IA11ba), (treo-2-IA11bb) ), (treo-2-IA11 bc) and (treo-2-IA11 bd), where each of the groups B ² , (R ¹ ) me (R ² ) n

265/289

R

R

O

(R), (treo-1-IA11 ba) R = OCH ₃ (treo-1-IA11bb) R = OC ₂ H ₅ (treo-1-IA11 bc) R = nC ₃ H ₇ (treo-2-IA11 ba ) R = OCH ₃ (treo-2-1 A11 bb) R = OC ₂ H ₅ (treo-2-IA11 bc) R = nC ₃ H ₇ (treo-2-1 A11 bd) R = iC ₃ H ₇ ( trec-1 - | A11 bd) R = iC ₃ H ₇ (treo-lA11 ba) = (treo-1 -IA11 ba) + (treo-2-lA11 ba) (50:50) = (rac.) (treo -lA11 bb) = (treo-1-IA11 bb) + (treo-2-IA11 bb) (50:50) = (rac.) (treo. | A11 bc) = (treo-1 -IA11 bc) + ( treo-2-LA11 bc) (50:50) = (rac.) (treo-IA11 bd) = (treo-1-IA11 bd) + (treo-2-IA11 bd) (50:50) = (rac. ) [739] For reference purposes, specific numbers (= example numbers) have been assigned to the compounds in Table 42a, where the number “treo-IA11 ba (line number)”, “treo-IA11bb (line number)” , “Treo-IA11bc (line number)” and “treo-IA11bd (line number)” refers to the racemic mixture of the treo enantiomers that have the chemical structure of the structural formulas (treo-1-IA11 ba) and (treo- 2-IA11ba), (treo-1-IA11bb) and (treo-2-IA11bb), (t reo-1-IA11bc) and (treo-2IA11bc) and (treo-1-IA11bd) and (treo-2-IA11bd), respectively, each presenting the structural combination of groups B ² , (R ¹ ) me (R ² ) n according to the line number in table 36.

[740] Correspondingly, in table 42b, the number “treo-2IA11ba (line number)”, “treo-2-IA11bb (line number)”, “treo-2IA11bc (line number)” or “ treo-2-IA11bd (line number) ”refers to the optically active treo-2 enantiomer in an enriched form [= form (2R, 3R) greater than 90% ee] which has the chemical structure of the structural formula (treo2- IA11ba (line number) ”,“ (treo-2-IA11bb (line number) ”,“ (treo-2IA11bc (line number) ”and“ (treo-2-IA11bd (line number) ”, respectively, each of them presenting the structural combination of groups B ² , (R ¹ ) me

266/289 (R ² ) n according to the line number in table 36.

[741] Table 42a (trematous racemates), examples:

[742] Compounds of structural formulas treo- (IA11ba), treo- (IA11bb), treo (IA11bc) and treo- (IA11bd), in each case in the form of racemic mixture of the treo isomers, in which the structural combination of the groups B ² , (R ¹ ) m (R ² ) n is defined according to a line number in Table 36. The individual compounds are numbered “treo-IA11 ba (line number)”, “treo-IA11 bb (number line) ”,“ treo-IA11bc (line number) ”and“ treo-IA11bd (line number) ”.

[743] Table 42b (optically active treo-2 enantiomers), examples:

[744] Optically active treo-2 enantiomers in an enriched form [= form (2R, 3R) greater than 90% ee] which have the chemical structure of the structural formula treo-2- (IA11ba), treo-2- (IA11bb) , treo-2- (IA11bc) or treo-2- (IA11bd), where the structural combination of groups B ² , (R ¹ ) m and (R ² ) n is defined according to a line number in table 36. The individual compounds are numbered "treo-2-IA11ba (line number)", "treo-2-IA11bb (line number)", "treo-2IA11bc (line number)" and "treo-2-IA11bd (number of line)".

[745] Table 42c, examples (optically active treo-1 enantiomers):

[746] Optically active treo-1 enantiomers in an enriched form [= form (2S, 3S) greater than 90% ee] which have the chemical structure of the structural formula treo-1- (IA11ba), treo-1- (IA11bb) , treo-1- (IA11bc) or treo-1- (IA11bd), where the structural combination of groups B ² , (R ¹ ) m and (R ² ) n is defined according to a line number in table 36. The individual compounds are numbered “treo-1-IA11ba (line number)”, “treo-1-IA11bb (line number)”, “treo-1IA11bc (line number)” and “treo-1-IA11bd (number of line)".

[747] Table 42d (erythro racemates), examples:

[748] Compounds of structural formulas erythro- (IA11 ba), erythro- (IA11 bb), erythro (IA11bc) and erythro- (IA11bd), in each case in the form of a racemic mixture of erythro isomers, in which the combination structural group B ² , (R ¹ ) m (R ² ) n is defined according to a line number in Table 36. The individual compounds are numbered “erythro-IA11ba (line number)”, “eritro267 / 289

IA11bb (line number) ”,“ eritro-IA11bc (line number) ”and“ eritroIA11bd (line number) ”.

[749] Table 42e (erythro-1 enantiomers), examples:

[750] Optically active erythro-2 enantiomers in an enriched form [= form (2R, 3S) greater than 90% ee] which have the chemical structure of the structural formula erythro-1- (IA11ba), erythro-1- (IA11bb) , erythro-1- (IA11bc) or erythro1- (IA11bd), where the structural combination of groups B ² , (R ¹ ) m and (R ² ) n is defined according to a line number in Table 36. The compounds individual numbers are numbered “eritro-1-IA11ba (line number)”, “eritro-1IA11bb (line number)”, “eritro-1-IA11bc (line number)” and “eritro-1IA11bd (line number)” .

[751] Table 42f (erythro-2 enantiomers) examples:

[752] Optically active erythro-2 enantiomers in an enriched form [= form (2S, 3R) greater than 90% ee] which have the chemical structure of the structural formula erythro-2- (IA11ba), erythro-2- (IA11bb) , erythro-2- (IA11bc) or erythro2- (IA11bd), where the structural combination of groups B ² , (R ¹ ) m and (R ² ) n is defined according to a line number in Table 36. The compounds individual numbers are numbered “eritro-2-IA11ba (line number)”, “eritro-2IA11bb (line number)”, “eritro-2-IA11bc (line number)” and “eritro-2IA11bd (line number)” .

[753] Physical data selected for examples in Tables 1 to 42f:

Testing methods

1) ¹ H-NMR data (400 MHz, CDCb); the characteristic chemical shifts [in ppm] are given for the example in question,

2) MS = mass spectrum, measured using a four pole instrument; electrospray ionization (+ -), mass range 100-1000; molecular peak M or [M + H] + or [M-1] + or [M-2] + or [M + 1] + indicated for the example in question,

3) HPLC = high performance liquid chromatography, column: Zorbax Eclipse, 50x3.0, C18 1.8 pm, mobile phase: water + 0.06% formic acid /

268/289 acrylonitrile + 0.06% formic acid, gradient: 90:10, after 2 minutes 5:95; detector: DAD (210 - 400 nm); retention time (tr) indicated for the example in question,

4) Chiral HPLC = HPLC on a chiral column, column: Chiralpak IC, 250 x 4.6mm, 5 pm DAIC 83325, detector wavelength: 210 nm; column temperature, flow and mobile phase indicated for the example in question.

Data for the examples

Example No. Iaa1 (mixture of erythro / threus 62:38 isomers):

[754] NMR (threus): 17.41 (s, 1H), 4.02 (d, 1H); NMR (erythro): 17.44 (s, 1H), 4.29 (d, 1H);

[755] MS: 412 [M + H] +; HPLC (tr): 1.67 minutes

Example No. IB9aa6 (54:46 erythro / threus mixture):

[756] NMR (threus): 13.54 (s, 1H); NMR (erythro): 13.64 (s, 1H); MS: 432 [M-1] +; HPLC (tr): 1.53 minutes

Example No. IB9aa1 (53:47 erythro / threus mixture):

[757] NMR (threo): 13.50 (s, 1H); NMR (erythro): 13.61 (s, 1H); MS: 430 [M-1] +; HPLC (tr): 1.59 minutes

Example No. IB9aa10 (60:40 mixture of erythro / threo isomers):

[758] NMR (threus): 13.54 (s, 1H); NMR (erythro): 13.63 (s, 1H); MS: 448 [M-2] +; HPLC (tr): 1.85 minutes

Example No. IB9aa20 (63:37 erythro / threo isomer mixture):

[759] NMR (threus): 17.46 (s, 1H), 4.03 (d, 1H); NMR (erythro): 17.47 (s, 1H), 4.30 (d, 1H);

[760] MS: 394 [M-1] +; HPLC (tr): 1.58 minutes

Example No. IB8aa10 (mixture of erythro / threo isomers at 57:43):

[761] NMR (threo): 13.56 (broad s, 1H), 3.99 (d, 1H), 3.83 (s, 3H); NMR (erythro): 13.56 (broad s, 1H), 4.09 (d, 1H), 3.85 (s, 3H); MS: 417 [M + 1] +; HPLC (tr): 1.53 minutes

Example No. IB8aa1 (mixture of erythro / threus isomers at 52:48):

269/289 [762] NMR (threo): 13.52 (broad s, 1H), 4.00 (d, 1H), 3.82 (s, 3H); NMR (erythro): 13.58 (broad s, 1H), 4.09 (d, 1H), 3.84 (s, 3H); MS: 383 [M + 1] +; HPLC (tr): 1.44 minutes

Example No. IB8aa43 (mixture of erythro / threus 59:41 isomers):

[763] NMR (erythro): 13.46 (broad s, 1H), 3.81 (s, 3H); NMR (threus): 13.55 (broad s, 1H), 3.84 (s, 3H); MS: 419 [M + 1] +; HPLC (tr): 1.46 minutes

Example No. IB9aa20 (59:41 mixture of erythro / threo isomers):

[764] NMR (threus): 13.51 (s, 1H); NMR (erythro): 13.62 (s, 1H);

[765] MS: 414 [M-1] +; HPLC (tr): 1.51 minutes

Example No. IBXaa20 (53:47 mixture of erythro / threo isomers):

[766] NMR (threus): 17.62 (s, 1H), 4.04 (d, 1H), 3.82 (s, 3H), 2.30 (s, 3H); NMR (erythro): 17.74 (s, 1H), 4.30 (d, 1H), 3.83 (s, 3H), 2.36 (s, 3H);

[767] MS: 398 [M-1] +; HPLC (tr): 1.65 minutes

Example No. IB8aa6 (57:43 mixture of erythro / threo isomers):

[768] NMR (threo): 17.62 (s, 1H), 4.04 (d, 1H), 3.82 (s, 3H), 2.30 (s, 3H); NMR (erythro): 13.62 (broad s, 1H), 4.10 (d, 1H), 3.85 (s, 3H); MS: 399 [M-1] +; HPLC (tr): 1.45 minutes

Example No. IB9aa25 (63:37 mixture of erythro / threo isomers):

[769] NMR (threus): 13.38 (s, 1H); NMR (erythro): 13.41 (s, 1H);

[770] MS: 430 [M-1] +; HPLC (tr): 1.58 minutes

Example No. IA12a57 (mixture of erythro / threus isomers at 63:37):

[771] NMR (threo): 3.99 (d, 1H), 3.76 (s, 3H), 3.67 (s, 3H), 1.11 (s, 9H); NMR (erythro): 4.30 (d, 1H), 3.84 (s, 3H), 3.73 (s, 3H), 1.17 (s, 9H);

Example No. Iaa95 (mixture of erythro / threus isomers at 57:43):

[772] NMR (threus): 17.27 (s, 1H); NMR (erythro): 17.35 (s, 1H);

[773] MS: 430 [M-1] +; HPLC (tr): 1.59 minutes

Example No. IB9aa23 (mixture of erythro / threus isomers at 58:42):

[774] NMR (threus): 13.43 (s, 1H); NMR (erythro): 13.53 (s, 1H);

[775] MS: 432 [M-1] +; HPLC (tr): 1.50 minutes

Example No. Iaa23 (mixture of erythro / threo isomers at 52:48):

270/289 [776] NMR (threus): 17.26 (s, 1H); NMR (erythro): 17.31 (s, 1H);

[777] MS: 414 [M + 1] +; HPLC (tr): 1.58 minutes

Example No. Iaa10 (mixture of erythro / threo isomers at 61:39):

[778] NMR (threus): 17.36 (s, 1H), 4.01 (d, 1H); NMR (erythro): 17.38 (s, 1H), 4.28 (d, 1H);

[779] MS: 430 [M + 1] +; HPLC (tr): 1.68 minutes

Example No. IB9ba6 (57:43 mixture of erythro / threo isomers):

[780] NMR (threus): 13.53 (s, 1H); NMR (erythro): 13.63 (s, 1H);

[781] MS: 460 [M-1] +; HPLC (tr): 1.67 minutes

Example No. IBXaa6 (57:43 mixture of erythro / threo isomers):

[782] NMR (threus): 17.59 (s, 1H), 4.02 (d, 1H), 3.83 (s, 3H), 2.31 (s, 3H); NMR (erythro): 17.67 (s, 1H), 4.30 (d, 1H), 3.83 (s, 3H), 2.36 (s, 3H);

[783] MS: 416 [M-1] +; HPLC (tr): 1.67 minutes

Example No. Iaa32 (mixture of erythro / threo isomers at 70:30):

[784] NMR (threus): 4.08 (d, 1H), 1.06 (s, 9H); NMR (erythro): 4.35 (d, 1H), 1.15 (s, 9H)

Example No. IA12aa23 (50:50 mixture of erythro / threo isomers):

[785] NMR (threus): 4.05 (d, 1H), 2.47 (s, 3H); NMR (erythro): 4.17 (d, 1H), 2.50 (s, 3H);

[786] MS: 588 [M + 1] +; HPLC (tr): 1.71 minutes

Example No. IA12ab53 (50:50 mixture of erythro / threo isomers):

[787] NMR (threus): 2.47 (s, 3H); NMR (erythro): 2.49 (s, 3H);

[788] MS: 616 [M + 1] +; HPLC (tr): 1.85 minutes

Example No. Ioa95 (50:50 mixture of erythro / threo isomers):

[789] NMR (threo): 13.8 (broad s, 1H), 3.80 (d, 1H); NMR (erythro): 13.8 (broad s, 1H), 4.18 (d, 1H);

[790] MS: 416 [M + 1] +; HPLC (tr): 1.39 minutes

Example No. Iaa53 (mixture of erythro / threo isomers at 60:34):

[791] NMR (threus): 4.07 (d, 1H), 1.08 (s, 9H); NMR (erythro): 4.35 (d, 1H), 1.16 (s, 9H)

271/289

Example No. IA12aa193 (57:43 mixture of erythro / threus isomers):

[792] NMR (threo): 3.74 (s, 3H), 3.67 (s, 3H), 1.15 (s, 9H); NMR (erythro): 3.78 (s, 3H), 3.68 (s, 3H), 1.19 (s, 9H);

Example No. IA12aa1 (mixture of erythro / threus isomers at 67:33):

[793] NMR (threo): 4.01 (d, 1H), 3.73 (s, 3H), 3.66 (s, 3H), 1.11 (s, 9H); NMR (erythro): 4.31 (d, 1H), 3.83 (s, 3H), 3.73 (s, 3H), 1.17 (s, 9H)

Example No. IA12aa78 (mixture of erythro / threus isomers at 66:34):

[794] NMR (threo): 4.11 (d, 1H), 3.79 (s, 3H), 3.66 (s, 3H), 1.14 (s, 9H); NMR (erythro): 4.30 (d, 1H), 3.81 (s, 3H), 3.71 (s, 3H), 1.19 (s, 9H)

Example No. IA12aa48 (mixture of erythro / threo isomers at 66:34):

[795] NMR (threo): 3.99 (d, 1H), 3.74 (s, 3H), 3.67 (s, 3H), 1.11 (s, 9H); NMR (erythro): 4.31 (d, 1H), 3.84 (s, 3H), 3.73 (s, 3H), 1.17 (s, 9H)

Example No. Ioa6 (mixture of erythro / threo isomers at 59:41):

[796] NMR (threo): 14.0 (broad s, 1H), 4.03 (d, 1H); NMR (erythro): 14.0 (broad s, 1H), 4.30 (d, 1H);

[797] MS: 400 [M + 1] +; HPLC (tr): 1.40 minutes

Example No. treo-IA12aa57 (treo racemate) [798] NMR (treo): 3.99 (d, 1H), 3.76 (s, 3H), 3.67 (s, 3H), 3.39 (m, 3H) , 1.11 (s, 9H) [799] chiral HPLC: flow rate: 1 ml / minute; column temperature: 30 ° C; mobile phase: A = n-heptane (80), B = isopropanol (20), retention time: treo-1: 10.751 minutes, treo-2: 10.801 minutes

Example No. erythro-2-IA12aa57 (optically active erythro-2 enantiomer) [800] NMR (erythro): 4.30 (d, 1H), 3.84 (s, 3H), 3.73 (s, 3H), 3, 35 (m, 1H), 3.21 (m, 1H), 3.07 (m, 1H), 1.17 (s, 9H);

[801] Chiral HPLC: flow rate: 1 ml / minute; column temperature: 30 ° C; mobile phase: A = n-heptane (80), B = isopropanol (20), retention time: 7.481 minutes

Example No. erythro-1-IA12aa57 (optically active erythro-1 enantiomer) [802] NMR (erythro): 4.30 (d, 1H), 3.84 (s, 3H), 3.73 (s, 3H), 3, 35 (m, 1H), 3.21

272/289 (m, 1H), 3.07 (m, 1H), 1.17 (s, 9H);

[803] Chiral HPLC: flow rate: 1 ml / minute; column temperature: 30 ° C; mobile phase: A = n-heptane (80), B = isopropanol (20), retention time: 6.036 minutes

Example No. IBXaa10 (mixture of erythro / threo isomers at 58:42):

[804] NMR (threo): 17.59 (s, 1H), 4.02 (d, 1H), 3.83 (s, 3H), 2.29 (s, 3H); NMR (erythro): 17.67 (s, 1H), 4.29 (d, 1H), 3.84 (s, 3H), 2.36 (s, 3H);

[805] MS: 432 [M + 1] +; HPLC (tr): 1.74 minutes

Example No. IBXaa43 (mixture of erythro / threus isomers at 73:27):

[806] NMR (threus): 17.54 (s, 1H), 4.18 (d, 1H), 3.79 (s, 3H), 2.32 (s, 3H); NMR (erythro): 17.59 (s, 1H), 4.30 (d, 1H), 3.88 (s, 3H), 2.35 (s, 3H);

[807] MS: 434 [M + 1] +; HPLC (tr): 1.66 minutes

Example No. Iaa83 (mixture of erythro / threo isomers at 61:39):

[808] NMR (threus): 17.26 (s, 1H); NMR (erythro): 17.37 (s, 1H);

[809] MS: 414 [M + 1] +; HPLC (tr): 1.57 minutes

Example No. Iea6 (mixture of erythro / threo isomers at 58:42):

[810] NMR (threo): 17.89 (m, 1H), 17.29 (s, 1H); NMR (erythro): 17.92 (m, 1H), 17.31 (s, 1H);

[811] MS: 442 [M + 1] +; HPLC (tr): 1.79 minutes

Example No. Ica6 (mixture of erythro / threus isomers at 64:36):

[812] NMR (threus): 17.35 (broad s, 1H), 4.01 (d, 1H); NMR (erythro): 17.36 (broad s, 1H), 4.29 (d, 1H);

[813] MS: 428 [M + 1] +; HPLC (tr): 1.70 minutes

Example No. treo-IA12aa48 (treo racemate) [814] NMR (treo): 3.99 (d, 1H), 3.75 (s, 3H), 3.67 (s, 3H), 3.39 (m, 3H) , 1.11 (s, 9H) [815] chiral HPLC: flow rate: 0.6 ml / minute; column temperature: 25 ° C; mobile phase: A = n-heptane (90), B = isopropanol (10), tr: treo-1: 34.839 minutes, treo2: 36.287 minutes

Example No. erythro-IA12aa48 (erythro racemate)

273/289 [816] NMR (erythro): 4.31 (d, 1H), 3.84 (s, 3H), 3.73 (s, 3H), 3.39 (m, 1H), 3.23 (m, 1H), 3.08 (m, 1H), 1.17 (s, 9H);

[817] Chiral HPLC: flow rate: 0.6 ml / minute; column temperature: 25 ° C; mobile phase: A = n-heptane (90), B = isopropanol (10), tr: erythro-1: 14,380 minutes, erythro-2: 17,766 min

Example No. Ifa6 (mixture of erythro / threus isomers at 64:36):

[818] NMR (threo): 17.41 (s, 1H), 4.00 (d, 1H), 1.06 (s, 3H), 1.03 (s, 3H); NMR (erythro): 17.42 (s, 1H), 4.29 (d, 1H), 1.08 (s, 3H), 1.05 (s, 3H);

[819] MS: 442 [M + 1] +; HPLC (tr): 1.75 minutes

Example No. treo-Iaa46 (treo racemate) [820] NMR (treo): 4.35 (d, 1H), 1.16 (s, 9H);

[821] Chiral HPLC: flow rate: 1 ml / minute; column temperature: 25 ° C; mobile phase: A = n-heptane (80), B = isopropanol (20), tr: treo-1: 13.092 minutes, treo2: 13.876 minutes

Example No. erythro-Iaa46 (erythro racemate) [822] NMR (threus): 4.08 (d, 1H), 1.09 (s, 9H);

[823] Chiral HPLC: flow rate: 1 ml / minute; column temperature: 25 ° C; mobile phase: A = n-heptane (80), B = isopropanol (20), tr: erythro-1: 10,151 minutes, erythro-2: 10,355

Example No. Iva6 (62:38 mixture of erythro / threo isomers):

[824] NMR (threus): 4.17 (d, 1H), 3.55 (s, 3H), 2.40 (s, 3H); NMR (erythro): 4.52 (d, 1H), 3.59 (s, 3H), 2.44 (s, 3H);

[825] MS: 414 [M + 1] +; HPLC (tr): 1.24 minutes

Example No. Ita6 (mixture of erythro / threus isomers at 66:34):

[826] NMR (threus): 7.60 (s, 1H), 4.15 (d, 1H), 3.62 (s, 3H); NMR (erythro): 7.66 (s, 1H), 4.45 (d, 1H), 3.66 (s, 3H);

[827] MS: 400 [M + 1] +; HPLC (tr): 1.31 minutes

Example No. IA12aa50 (mixture of erythro / threo isomers at 57:43):

[828] NMR (treo): 2.15 (q, 2H), 1.03 (t, 3H); NMR (erythro): 2.36 (q, 2H), 1.13 (t, 3H);

274/289

Example No. IB9aa49 (mixture of erythro / threus 59:41 isomers):

[829] NMR (threus): 1.91 (s, 3H); NMR (erythro): 2.12 (s, 3H);

Example No. Iea95 (mixture of erythro / threo isomers at 58:42):

[830] NMR (threus): 17.20 (m, 1H); NMR (erythro): 17.83 (m, 1H);

[831] MS: 460 [M + 1] +; HPLC (tr): 1.78 minutes

Example No. treo-Iva48 (treo racemate) [832] NMR (treo): 4.17 (d, 1H), 3.85 (m, 1H), 3.59 (s, 3H), 2.78 (q, 2H) , 2.36 (s, 3H), 1.33 (t, 3H)

Example No. erythro-Ivva48 (erythro racemate) [833] NMR (threus): 6.72 - 7.20 (m, 7H), 4.50 (d, 1H), 3.71 (m, 1H), 3.62 ( s, 3H), 3.41 (m, 1H), 3.11 (m, 1H), 2.79 (q, 2H), 2.47 (s, 3H), 1.33 (t, 3H)

Example No. Ifa95 (mixture of erythro / threo isomers at 61:39):

[834] NMR (threus): 17.30 (s, 1H), 2.47 (s, 3H), 2.30 (s, 3H); NMR (erythro): 17.39 (s, 1H), 2.51 (s, 3H), 2.37 (s, 3H);

[835] MS: 460 [M + 1] +; HPLC (tr): 1.74 minutes

Example No. Ita95 (mixture of erythro / threus isomers at 73:27):

[836] NMR (treo): 7.80 (s, 1H), 4.17 (d, 1H), 3.67 (s, 3H), 2.72 (q, 2H), 1.30 (t, 3H); NMR (erythro): 7.90 (s, 1H), 4.45 (d, 1H), 3.71 (s, 3H), 2.80 (q, 2H), 1.35 (t, 3H);

Example No. Iva6 (mixture of erythro / threo isomers at 51:49):

[837] NMR (threus): 4.18 (d, 1H), 2.35 (s, 3H); NMR (erythro): 4.38 (d, 1H), 2.45 (s, 3H);

[838] MS: 432 [M + 1] +; HPLC (tr): 1.67 minutes

Example No. Ica95 (mixture of erythro / threo isomers at 58:42):

[839] NMR (threus): 17.23 (m, 1H); NMR (erythro): 17.31 (m, 1H);

[840] MS: 446 [M + 1] +; HPLC (tr): 1.22 minutes

Example No. Iga95 (mixture of erythro / threo isomers at 57:43):

[841] NMR (threus): 17.62 (s, 1H); NMR (erythro): 17.69 (s, 1H);

[842] MS: 502 [M + 1] +; HPLC (tr): 1.68 minutes

Example No. Iva259 (52:48 mixture of erythro / threus isomers):

275/289 [843] NMR (treo): 4.29 - 4.37 (m, 1H), 4.13 (d, 1H), 3.59 (s, 3H), 2.80 (q, 2H) , 2.37 (s, 3H), 1.35 (t, 3H); NMR (erythro): 4.37 (d, 1H), 3.60 (s, 3H), 2.80 (q, 2H), 2.42 (s, 3H), 1.35 (t, 3H);

Example No. Iaa6 (mixture of erythro / threo isomers at 61:39):

[844] NMR (threus): 17.38 (s, 1H), 4.01 (d, 1H); NMR (erythro): 17.39 (s, 1H), 4.30 (d, 1H);

[845] MS: 413 [M + 1] +; HPLC (tr): 1.52 minutes

Example No. IB9aa43 (62:38 mixture of erythro / threus isomers):

[846] NMR (threus): 13.37 (s, 1H); NMR (erythro): 13.41 (s, 1H);

[847] MS: 450 [M + 1] +; HPLC (tr): 1.51 minutes

Example No. treo-2-IB8aa43 (treo racemate) [848] NMR (treo): 13.55 (s, 1H), 7.17 (m, 1H), 7.02 (m, 2H), 6.92 (m, 1H), 6.77 (t, 2H), 4.23 (d, 1H), 4.19 (m, 1H), 3.84 (s, 3H), 3.47 (m, 2H);

[849] MS: 419 [M + 1] +; HPLC (tr): 1.51 minutes; optical rotation: [a] D ²⁰ = -52.295 in CHCl 3, (concentration = 2.157 g / mL).

Example No. Ioa83 (mixture of erythro / threo isomers at 53:47):

[850] NMR (threo): 13.8 (broad s, 1H), 6.72 (t, 1H); NMR (erythro): 13.8 (broad s, 1H), 6.89 (t, 1H);

[851] MS: 400 [M + 1] +; HPLC (tr): 1.39 minutes

Example No. Ioa29 (mixture of erythro / threo isomers at 60:40):

[852] NMR (threo): 13.8 (broad s, 1H), 4.27 (d, 1H); NMR (erythro): 13.8 (broad s, 1H), 4.01 (d, 1H);

[853] MS: 382 [M + 1] +; HPLC (tr): 1.43 minutes

Example No. Ioa24 (60:40 mixture of erythro / threus isomers):

[854] NMR (threus): 13.8 (broad s, 1H), 4.36 (d, 1H); NMR (erythro): 13.8 (broad s, 1H), 4.71 (d, 1H);

[855] MS: 418 [M + 1] +; HPLC (tr): 1.44 minutes

Example No. Ioa3 (60:40 mixture of erythro / threo isomers):

[856] NMR (threus): 13.8 (broad s, 1H), 4.26 (d, 1H); NMR (erythro): 13.8 (broad s, 1H), 3.99 (d, 1H);

276/289 [857] MS: 416 [M + 1] +; HPLC (tr): 1.54 minutes

Example No. Ioa17 (mixture of erythro / threo isomers at 58:42):

[858] NMR (threo): 13.8 (broad s, 1H), 4.22 (d, 1H); NMR (erythro): 13.8 (broad s, 1H), 4.00 (d, 1H);

[859] MS: 400 [M + 1] +; HPLC (tr): 1.54 minutes

Example No. Ioa2 (mixture of erythro / threo isomers at 58:42):

[860] NMR (treo): 13.8 (broad s, 1H), 4.27 (d, 1H); NMR (erythro): 13.8 (broad s, 1H), 4.04 (d, 1H);

[861] MS: 382 [M + 1] +; HPLC (tr): 1.40 minutes

Example No. Ioa9 (63:37 erythro / threus mixture isomers):

[862] NMR (threo): 13.8 (broad s, 1H), 4.25 (d, 1H); NMR (erythro): 13.8 (broad s, 1H), 4.03 (d, 1H);

[863] MS: 398 [M + 1] +; HPLC (tr): 1.49 minutes

Example No. Ioa20 (63:37 mixture of erythro / threus isomers):

[864] NMR (threo): 13.8 (broad s, 1H), 4.26 (d, 1H); NMR (erythro): 13.8 (broad s, 1H), 4.02 (d, 1H);

[865] MS: 382 [M + 1] +; HPLC (tr): 1.40 minutes

Example No. Ioa1 (63:37 mixture of erythro / threo isomers):

[866] NMR (treo): 13.8 (broad s, 1H), 4.26 (d, 1H); NMR (erythro): 13.8 (broad s, 1H), 4.03 (d, 1H);

[867] MS: 398 [M + 1] +; HPLC (tr): 1.50 minutes

Example No. Ica83 (63:37 mixture of erythro / threus isomers):

[868] NMR (threus): 6.70 (t, 2H); NMR (erythro): 6.88 (t, 2H);

[869] MS: 428 [M + 1] +; HPLC (tr): 1.68 minutes

Example No. Ifa83 (64:36 mixture of erythro / threo isomers):

[870] NMR (threus): 6.70 (t, 2H); NMR (erythro): 6.88 (t, 2H);

[871] MS: 442 [M + 1] +; HPLC (tr): 1.74 minutes

Example No. Iea83 (mixture of erythro / threus isomers at 67:33):

[872] NMR (threus): 6.70 (t, 2H); NMR (erythro): 6.88 (t, 2H);

[873] MS: 442 [M + 1] +; HPLC (tr): 1.79 minutes

277/289

Example No. Ica29 (mixture of erythro / threus isomers at 63:37):

[874] NMR (threo): 4.01 (m, 1H); NMR (erythro): 4.30 (m, 1H);

[875] MS: 410 [M + 1] +; HPLC (tr): 1.73 minutes

Example No. Ifa29 (62:38 mixture of erythro / threus isomers):

[876] NMR (threus): 4.01 (d, 1H); NMR (erythro): 4.30 (m, 1H);

[877] MS: 424 [M + 1] +; HPLC (tr): 1.79 minutes

Example No. Iea29 (mixture of erythro / threo isomers at 61:39):

[878] NMR (threus): 4.01 (d, 1H); NMR (erythro): 4.31 (dd, 1H);

[879] MS: 424 [M + 1] +; HPLC (tr): 1.83 minutes

Example No. Iaa29 (mixture of erythro / threus isomers at 62:38):

[880] NMR (threus): 4.01 (d, 1H); NMR (erythro): 4.31 (m, 1H);

[881] MS: 396 [M + 1] +; HPLC (tr): 1.63 minutes

Example No. Ica3 (62:38 mixture of erythro / threus isomers):

[882] NMR (threo): 3.98 (dd, 1H); NMR (erythro): 4.29 (d, 1H);

[883] MS: 444 [M + 1] +; HPLC (tr): 1.82 minutes

Example No. Ifa3 (62:38 mixture of erythro / threus isomers):

[884] NMR (treo): 3.99 (dd, 1H); NMR (erythro): 4.29 (d, 1H);

[885] MS: 458 [M + 1] +; HPLC (tr): 1.88 minutes

Example No. Iea3 (64:36 mixture of erythro / threus isomers):

[886] NMR (treo): 4.00 (dd, 1H); NMR (erythro): 4.31 (dd, 1H);

[887] MS: 458 [M + 1] +; HPLC (tr): 1.91 minutes

Example No. Iaa3 (64:36 erythro / threus mixture isomers):

[888] NMR (treo): 4.00 (d, 1H); NMR (erythro): 4.29 (d, 1H);

[889] MS: 430 [M + 1] +; HPLC (tr): 1.73 minutes

Example No. Ica25 (mixture of erythro / threus isomers at 63:37):

[890] NMR (treo): 4.08 (m, 1H); NMR (erythro): 4.34 (d, 1H);

[891] MS: 446 [M + 1] +; HPLC (tr): 1.73 minutes

Example No. Ifa25 (64:36 mixture of erythro / threus isomers):

[892] NMR (threo): 4.08 (m, 1H), 2.35 (s, 2H); NMR (erythro): 4.34 (d, 1H), 2.51 (s, 2H);

278/289 [893] MS: 460 [M + 1] +; HPLC (tr): 1.78 minutes

Example No. Iea25 (mixture of erythro / threo isomers at 59:41):

[894] NMR (treo): 4.08 (m, 1H), 2.51 (m, 2H); NMR (erythro): 4.34 (d, 1H), 2.68 (m, 2H);

[895] MS: 460 [M + 1] +; HPLC (tr): 1.82 minutes

Example No. Ica17 (mixture of erythro / threus isomers at 54:46):

[896] NMR (treo): 4.09 (m, 1H), 2.55 (m, 2H); NMR (erythro): 4.36 (d, 1H), 2.65 (m, 2H);

[897] MS: 428 [M + 1] +; HPLC (tr): 1.72 minutes

Example No. Ifa17 (mixture of erythro / threo isomers at 57:43):

[898] NMR (threo): 2.48 (s, 2H); NMR (erythro): 4.36 (d, 1H), 2.52 (s, 2H);

[899] MS: 442 [M + 1] +; HPLC (tr): 1.78 minutes

Example No. Iea17 (mixture of erythro / threus isomers at 56:44):

[900] NMR (threus): 2.51 (s, 2H); NMR (erythro): 2.66 (s, 2H);

[901] MS: 443 [M + 2] +; HPLC (tr): 1.82 minutes

Example No. Iaa17 (mixture of erythro / threo isomers at 51:49):

[902] NMR (threo): 2.48 (m, 2H); NMR (erythro): 4.36 (d, 1H), 2.63 (m, 2H);

[903] MS: 414 [M + 1] +; HPLC (tr): 1.63 minutes

Example No. Ica23 (mixture of erythro / threo isomers at 54:46):

[904] NMR (threus): 4.12 (d, 1H), 2.53 (m, 2H); NMR (erythro): 4.32 (d, 1H), 2.67 (m, 2H);

[905] MS: 428 [M + 1] +; HPLC (tr): 1.70 minutes

Example No. Ifa23 (56:44 mixture of erythro / threus isomers):

[906] NMR (threus): 4.13 (d, 1H), 2.49 (s, 2H); NMR (erythro): 4.33 (d, 1H), 2.51 (s, 2H);

[907] MS: 442 [M + 1] +; HPLC (tr): 1.76 minutes

Example No. Iea23 (mixture of erythro / threo isomers at 60:40):

[908] NMR (threo): 2.51 (m, 2H); NMR (erythro): 2.68 (m, 2H);

[909] MS: 442 [M + 1] +; HPLC (tr): 1.79 minutes

Example No. Ica2 (mixture of erythro / treo isomers at 65:35):

279/289 [910] NMR (threus): 4.03 (dd, 1H); NMR (erythro): 4.30 (d, 1H);

[911] MS: 410 [M + 1] +; HPLC (tr): 1.70 minutes

Example No. Iea2 (mixture of erythro / threo isomers at 60:40):

[912] NMR (threus): 4.02 (d, 1H), 2.48 (s, 2H); NMR (erythro): 4.31 (d, 1H), 2.52 (s, 2H);

[913] MS: 424 [M + 1] +; HPLC (tr): 1.76 minutes

Example No. Iea9 (62:38 mixture of erythro / threo isomers):

[914] NMR (treo): 4.03 (dd, 1H), 2.51 (m, 2H); NMR (erythro): 4.31 (dd, 1H), 2.67 (m, 2H);

[915] MS: 440 [M + 1] +; HPLC (tr): 1.87 minutes

Example No. Ifa9 (62:38 mixture of erythro / threus isomers):

[916] NMR (threus): 4.03 (d, 1H), 2.49 (s, 2H); NMR (erythro): 4.29 (d, 1H), 2.52 (s, 2H);

[917] MS: 440 [M + 1] +; HPLC (tr): 1.83 minutes

Example No. Iaa9 (60:40 mixture of erythro / threus isomers):

[918] NMR (threus): 4.03 (d, 1H), 2.48 (m, 2H); NMR (erythro): 4.29 (d, 1H), 2.64 (m, 2H);

[919] MS: 412 [M + 1] +; HPLC (tr): 1.68 minutes

Example No. Ica20 (64:36 mixture of erythro / threus isomers):

[920] NMR (treo): 4.02 (dd, 1H), 2.54 (m, 2H); NMR (erythro): 4.29 (d, 1H), 2.66 (m, 2H);

[921] MS: 410 [M + 1] +; HPLC (tr): 1.71 minutes

Example No. Ifa20 (64:36 mixture of erythro / threo isomers):

[922] NMR (threus): 4.02 (d, 1H), 2.48 (s, 2H); NMR (erythro): 4.30 (d, 1H), 2.52 (s, 2H);

[923] MS: 424 [M + 1] +; HPLC (tr): 1.76 minutes

Example No. Iea20 (59:41 mixture of erythro / threo isomers):

[924] NMR (treo): 4.02 (dd, 1H), 2.51 (m, 2H); NMR (erythro): 4.32 (dd, 1H), 2.68 (m, 2H);

[925] MS: 424 [M + 1] +; HPLC (tr): 1.81 minutes

280/289

Example No. Ica1 (mixture of erythro / threus isomers at 63:37):

[926] NMR (threo): 4.02 (dd, 1H); NMR (erythro): 4.29 (d, 1H);

[927] MS: 426 [M + 1] +; HPLC (tr): 1.79 minutes

Example No. Ifa (62:38 mixture of erythro / threus isomers):

[928] NMR (threus): 4.01 (d, 1H), 2.48 (s, 2H); NMR (erythro): 4.29 (d, 1H), 2.52 (s, 2H);

[929] MS: 440 [M + 1] +; HPLC (tr): 1.85 minutes

Example No. Iea1 (68:32 mixture of erythro / threus isomers):

[930] NMR (treo): 4.02 (dd, 1H), 2.50 (m, 2H); NMR (erythro): 4.32 (dd, 1H), 2.67 (m, 2H);

[931] MS: 440 [M + 1] +; HPLC (tr): 1.89 minutes

Example No. Iga95 (68:32 mixture of erythro / threus isomers):

[932] NMR (treo): 4.02 (dd, 1H), 2.50 (m, 2H); NMR (erythro): 4.32 (dd, 1H), 2.67 (m, 2H);

[933] MS: 502 [M + 1] +; HPLC (tr): 1.83 minutes

Example No. Iva83 (mixture of erythro / threus isomers at 51:49):

[934] NMR (threus): 4.21 (d, 1H), 3.53 (s, 3H), 2.31 (s, 3H); NMR (erythro): 3.53 (s, 3H), 2.45 (s, 3H);

[935] MS: 414 [M + 1] +; HPLC (tr): 1.20 minutes

Example No. Iva24 (mixture of erythro / threus isomers at 64:36):

[936] NMR (threus): 3.58 (s, 3H), 2.45 (s, 3H); NMR (erythro): 4.55 (d, 1H), 3.54 (s, 3H), 2.31 (s, 3H);

[937] MS: 432 [M + 1] +; HPLC (tr): 1.27 minutes

Example No. Iva3 (mixture of erythro / threo isomers at 72:28):

[938] NMR (threus): 4.17 (d, 1H), 3.54 (s, 3H), 2.39 (s, 3H); NMR (erythro): 4.51 (d, 1H), 3.59 (s, 3H), 2.44 (s, 3H);

[939] MS: 430 [M + 1] +; HPLC (tr): 1.36 minutes

Example No. Iva17 (mixture of erythro / threus isomers at 72:28):

[940] NMR (threus): 4.24 (d, 1H), 3.51 (s, 3H), 2.42 (s, 3H); NMR (erythro): 4.55 (d, 1H), 3.55 (s, 3H), 2.41 (s, 3H);

281/289 [941] MS: 414 [M + 1] +; HPLC (tr): 1.25 minutes

Example No. Iva2 (mixture of erythro / threo isomers at 71:29):

[942] NMR (threo): 4.19 (d, 1H), 3.54 (s, 3H), 2.40 (s, 3H); NMR (erythro): 4.51 (d, 1H), 3.59 (s, 3H), 2.44 (s, 3H);

[943] MS: 397 [M + 2] +; HPLC (tr): 1.22 minutes

Example No. Iva9 (mixture of erythro / threo isomers at 71:29):

[944] NMR (threo): 4.19 (d, 1H), 3.54 (s, 3H), 2.40 (s, 3H); NMR (erythro): 4.51 (d, 1H), 3.58 (s, 3H), 2.44 (s, 3H);

[945] MS: 412 [M + 1] +; HPLC (tr): 1.26 minutes

Example No. Iva20 (mixture of erythro / threo isomers at 71:29):

[946] NMR (threus): 4.19 (d, 1H), 3.54 (s, 3H), 2.39 (s, 3H); NMR (erythro): 4.50 (d, 1H), 3.59 (s, 3H), 2.44 (s, 3H);

[947] MS: 397 [M + 2] +; HPLC (tr): 1.22 minutes

Example No. Iva1 (mixture of erythro / threo isomers at 71:29):

[948] NMR (threus): 4.18 (d, 1H), 3.53 (s, 3H), 2.38 (s, 3H); NMR (erythro): 4.51 (d, 1H), 3.58 (s, 3H), 2.43 (s, 3H);

[949] MS: 412 [M + 1] +; HPLC (tr): 1.32 minutes

Example No. IB10ga6 (62:38 mixture of erythro / threo isomers):

[950] NMR (treo): 8.48 (s, 1H), 7.27 (m, 1H), 7.12 (m, 1H), 6.96 (m, 5H), 4.13 (d, 1H), 3.82 (m, 1H), 3.39 (dd, 1H), 3.23 (dd, 1H), 2.65 (s, 3H);

[951] MS: 385 [M + 1] +; HPLC (tr): 1.57 minutes;

[952] NMR (erythro): 8.54 (s, 1H), 7.22 (m, 1H), 7.09 (m, 1H), 6.98 (m, 2H), 6.82 (m, 3H), 4.51 (d, 1H), 3.71 (m, 1H), 3.50 (dd, 1H), 3.27 (dd, 1H), 2.75 (s, 3H);

[953] MS: 385 [M + 1] +; HPLC (tr): 1.57 minutes

Example No. erythro-2-IB10ga6 (optically active erythro-2 isomer) [954] NMR (erythro): 8.54 (s, 1H), 7.22 (m, 1H), 7.09 (m, 1H), 6, 98 (m, 2H), 6.82 (m, 3H), 4.51 (d, 1H), 3.71 (m, 1H), 3.50 (dd, 1H), 3.27 (dd, 1H ), 2.75 (s, 3H);

[955] MS: 385 [M + 1] +; HPLC (tr): 1.57 minutes

Example No. erythro-1-IB10ga6 (optically active erythro-1 isomer) [956] NMR (erythro): 8.54 (s, 1H), 7.22 (m, 1H), 7.09 (m, 1H), 6, 98 (m, 2H), 6.82

282/289 (m, 3H), 4.51 (d, 1H), 3.71 (m, 1H), 3.50 (dd, 1H), 3.27 (dd, 1H), 2.75 (s , 3H);

MS: 385 [M + 1] +; HPLC (tr): 1.57 minutes

Example No. treo-2- IB10ga6 (optically active treo-1 isomer):

[957] NMR (treo): 8.48 (s, 1H), 7.27 (m, 1H), 7.12 (m, 1H), 6.96 (m, 5H), 4.13 (d, 1H), 3.82 (m, 1H), 3.39 (dd, 1H), 3.23 (dd, 1H), 2.65 (s, 3H);

[958] MS: 385 [M + 1] +; HPLC (tr): 1.57 minutes

Example No. IA12aa194 (mixture of erythro / threo isomers at 80:20):

[959] NMR (threus): 4.24 (d, 1H), 2.04 (s, 3H); NMR (erythro): 4.16 (d, 1H), 2.02 (s, 3H);

[960] MS: 452 [M-42] +; HPLC (tr): 1.57 minutes

Example No. eritro-IA12aa49:

[961] NMR (erythro): 4.33 (d, 1H), 3.87 (s, 3H), 3.76 (s, 3H), 2.12 (s, 3H);

[962] MS: 434 [M-42] +; HPLC (tr): 1.57 minutes

Example No. treo-1-IA12aa49:

[963] NMR (treo1): 3.95 (d, 1H), 3.75 (s, 3H), 3.96 (s, 3H), 1.91 (s, 3H);

[964] MS: 434 [M-42] +; HPLC (tr): 1.57 minutes

Example No. treo-2-IB12aa49:

[965] NMR (treo2): 3.95 (d, 1H), 3.75 (s, 3H), 3.96 (s, 3H), 1.91 (s, 3H);

[966] MS: 434 [M-42] +; HPLC (tr): 1.57 minutes (B) Formulation examples [967] a) A dust is obtained by mixing 10 parts by weight of a compound of formula (I) and 90 parts by weight of talc, while inert substance, and mix the mixture in a hammer mill.

[968] b) A humectable powder is obtained which is easily dispersible in water by mixing 25 parts by weight of a compound of structural formula (I), 64 parts by weight of quartz containing kaolin as an inert substance, 10 parts by weight of potassium lignosulphonate and 1 part by weight of sodium oleoylmethyltaurate, as a wetting and dispersing agent, and the mixture is ground in a pin disc mill.

[969] c) A water-dispersible dispersion concentrate is obtained by

283/289 mixture of 20 parts by weight of a compound of structural formula (I) with 6 parts by weight of alkylphenyl-polyglycolic ether (®Triton X 207), 3 parts by weight of isotridecanol-polyglycolic ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling point, for example, between 255 ° C and above 277 ° C) and the mixture is ground in a ball mill to a fineness of less than 5 microns.

[970] d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of structural formula (I), 75 parts by weight of cyclohexanone, as a solvent, and 10 parts by weight of oxyethylated nonylphenol, while emulsifier.

[971] e) Water-dispersible granules are obtained by mixing parts by weight of a compound of structural formula (I), parts by weight of calcium lignosulphonate, parts by weight of sodium lauryl sulphate, parts by weight of polyvinyl alcohol and parts by weight of kaolin, grinding the mixture in a pin disc mill and granulating the powder in a fluidized bed by spraying water as the granulation liquid.

[972] f) Water-dispersible granules are also obtained by homogenizing and pre-comminution of parts by weight of a compound of structural formula (I), parts by weight of 2,2'-dinaftymethane-6,6'-disulfonate sodium, parts by weight of sodium oleoylmethyltaurinate, parts by weight of polyvinyl alcohol, parts by weight of calcium carbonate and parts by weight of water, in a colloid mill, subsequent grinding of the mixture in a ball mill and atomisation and drying of the suspension resulting in a spray tower by means of an injector for individual substances.

(C) Biological examples

284/289

Pre-emergence herbicidal action [973] Seeds of monocotyledonous and dicotyledonous weed plants and crop plants were placed in woody fiber pots on sandy loamy soil and covered with soil. The compounds (I) according to the invention, formulated in the form of wettable powders (WP), were then applied in the form of an aqueous suspension or emulsion at a water application rate of 600 L / ha (converted) with the addition of 0.2% of wetting agent to the cover soil surface.

[974] After the treatment, the pots were placed in a greenhouse and kept under good growing conditions for the test plants. After about 3 weeks, the effect of the preparations was visually classified, compared to untreated controls, as percentages. For example, 100% activity = plants have died, 50% activity or herbicide damage = plants have been reduced by 50% or plant mass has been reduced by 50%, 0% activity = equal to control plants.

[975] The compounds (I) according to the invention, such as, for example, compounds ^Nos. IA12a57, IA12aa1, IA12aa193, IA12aa23, IA12aa48, IA12aa50, IA12aa78, IA12ab53, Iaa1, Iaa10, Iaa20, Iaa23, Iaa32, Iaa53, Iaa6, Iaa, IBa, IBa, Iaa, IBa, Iaa, IBa, IB9aa25, IB9aa43, IB9aa49, IB9aa6, IB9ba6, IBXaa10, IBXaa20, IBXaa43, IBXaa6, Ica6, Ica95, Iea6, Iea95, Ifa6, Ifa95, Iga95, Ioa6, Ioa95, Ita6, I6, I6 IB10ga6, eritro-2-IB10ga6, eritro-IA12aa49, IA12aa194, Iaa17, Iaa29, Iaa3, Ica83, Iaa9, IB10ga6, treo-2-IB8aa43, Ica1, Ica17, Ica2, Ica20, Ica23, Ica3 Iea17, Iea2, Iea20, Iea23, Iea25, Iea29, Iea3, Iea83, Iea9, Ifa1, Ifa17, Ifa20, Ifa23, Ifa25, Ifa29, Ifa3, Ifa83, Ifa9, Iga95, Ioa1, Ioa17, Ioa2, Ioa20, Ioa24 Ioa3, Ioa83, Ioa9, Iva1, Iva17, Iva2, Iva20, Iva24, Iva3, Iva83, Iva9, treo-1-IA12aa49, treo-2-IB10ga6 and treo-2IB12aa49 of tables 1 to 42f, in the form of an erythro mixture / treus or treo racemates or treo-2 enantiomers, showed good herbicidal efficacy a (70% to 100% activity) against several harmful plants for

285/289 an application rate of 320 g or less of active substance per hectare, when applied by the pre-emergence method.

[976] For example, compounds ^Nos. Iaa20, Iaa23, Iaa53, Iaa95, Ioa95, IA12aa78, IB9aa6, IB9ba6, IB9aa10, IB9aa23, IB9aa25, IB9aa43, treo-2IB8aa43, treo-1-IA12aa49, IA12aa19a, Iaaa % -100%) against harmful plants, such as Viola tricolor, when applied by the pre-emergence method at an application rate of 0.32 kg of active substance per hectare.

[977] For example, compounds ^Nos. IA12aa78, IB9aa6, IB9aa25, IB9aa43, IB9ba6, treo-2-IB8aa43, IVa9 and IA12aa194 also show very good activity (90% -100%) against harmful plants, such as Stellaria media, when applied by the pre-emergence method to an application rate of 0.32 kg of active substance per hectare.

[978] For example, compounds ^Nos. Iaa95, IA12aa78, IB9aa6, IB9aa10, IB9aa25, treo-2-IB8aa43, IB9aa43 and IB9ba6 also show very good activity (80% -100%) against harmful plants, such as, Stellaria media, when applied by the pre-emergence method at an application rate of 0.32 kg of active substance per hectare.

[979] For example, compounds ^Nos. Iaa23, Iaa53, IB9aa1, IB9aa10, IB9aa25, IB9aa23, IB9aa43, Ioa95, Ioa2, Iea1, Ioa9, treo-2-IB8aa43, treo-1-IA12aa49 and IA12aa194 also show very good activity (80% -100%) harmful, such as Polygonum convolvulus, when applied by the pre-emergence method at an application rate of 0.32 kg of active substance per hectare.

[980] For example, compounds ^Nos. Iaa95, IB9aa6, IB9aa10, IB9aa25, IB9aa1, IB9aa43, Iea29, treo-2-IB8aa43, treo-1-IA12aa49 and IA12aa194 also show very good activity (80% -100%) against harmful plants, such as Amarantus retroflexus, when applied by the preemergence method at an application rate of 0.32 kg of active substance per hectare.

[981] For example, compounds ^Nos. Iaa23, Iaa95, IB9aa23, IB9aa25, IB9aa6,

286/289

IB9ba6 and IB9aa43 also show very good activity (80% -100%) against harmful plants, such as Setaria viridis, when applied by the pre-emergence method at an application rate of 0.32 kg of active substance per hectare.

[982] For example, compounds ^Nos. Iaa95, IB9aa25, IB9aa1, IB9aa43, Ica2, treo-2-IB8aa43, treo-1-IA12aa49 and IA12aa194 also show very good activity (80% -100%) against harmful plants, such as Alopecurus myosuroides, when applied by the method of pre-emergence at an application rate of 0.32 kg of active substance per hectare.

[983] For example, compounds ^Nos. Ioa83 and treo-1-IA12aa49 also show very good activity (80% -100%) against harmful plants, such as Abuthilon theophrasti, when applied by the preemergence method at an application rate of 0.32 kg of active substance per hectare .

[984] For example, compounds ^Nos. Ica2, Iea23, Iaa17, IA12aa194 and treo-1IA12aa49 also show very good activity (80% -100%) against harmful plants, such as Veronica persica, when applied by the pre-emergence method at an application rate of 0.32 kg of active substance per hectare.

[985] For example, compounds ^Nos. Ica17, Iva25 and treo-1-IA12aa49 also show very good activity (80% -100%) against harmful plants, such as Veronica persica, when applied by the pre-emergence method at an application rate of 0.32 kg. active substance per hectare.

2. Post-emergence herbicidal action [986] Seeds of monocotyledonous and dicotyledonous weeds and crop plants were placed in woody fiber pots on sandy loamy soil, covered with soil and grown in a greenhouse under good conditions. growth. Two to three weeks after cultivation, the test plants were treated in a leaf condition, in which the compounds (I) according to the invention, formulated in the form of humectable powders, were applied by spraying in the form of of an aqueous suspension or emulsion at a rate of

287/289 application of water of 600 L / ha (converted) with the addition of 0.2% of humectant to the green parts of the plants. After keeping the plants in the greenhouse under optimal growth conditions for about 3 weeks, the activity of the preparations was visually classified, compared to untreated controls, in percentage (%). For example, 100% activity = plants have died, 50% activity or herbicidal damage = plants have been reduced by 50% or plant mass has been reduced by 50%, 0% activity = equal to control plants.

[987] As seen from the results, the compounds (I) according to the invention, such as, for example, compounds ^Nos. IA12a57, IA12aa1, IA12aa193, IA12aa23, IA12aa48, IA12aa50, IA12aa78, IA12ab53, Iaa1, Iaa10, Iaa20, Iaa23, Iaa32, Iaa53, Iaa6, Iaa, IBa, IBa, Iaa, IBa, Iaa, IBa, IB9aa25, IB9aa43, IB9aa49, IB9aa6, IB9ba6, IBXaa10, IBXaa20, IBXaa43, IBXaa6, Ica6, Ica95, Iea6, Iea95, Ifa6, Ifa95, Iga95, Ioa6, Ioa95, Ita6, I6, I6 IB10ga6, eritro-2-IB10ga6, eritro-IA12aa49, IA12aa194, Iaa17, Iaa29, Iaa3, Ica83, Iaa9, IB10ga6, treo-2-IB8aa43, Ica1, Ica17, Ica2, Ica20, Ica23, Ica3 Iea17, Iea2, Iea20, Iea23, Iea25, Iea29, Iea3, Iea83, Iea9, Ifa1, Ifa17, Ifa20, Ifa23, Ifa25, Ifa29, Ifa3, Ifa83, Ifa9, Iga95, Ioa1, Ioa17, Ioa2, Ioa20, Ioa24 Ioa3, Ioa83, Ioa9, Iva1, Iva17, Iva2, Iva20, Iva24, Iva3, Iva83, Iva9, treo-1-IA12aa49, treo-2- IB10ga6 and treo-2-IB12aa49 in tables 1 to 42f above, in the form of mixture erythro / treo or raceo treo or enantiomers treo-2, present a good herbicidal efficacy (7 0% to 100% activity) against various harmful plants at an application rate of 320 g or less of active substance per hectare, when applied by the post-emergence method.

[988] In this case, for example, compounds ^Nos. IB9aa6, Iaa1, Iaa20, IB9ba6, IB9aa10, IB9aa1, IB9aa23, IB9aa25, IB9aa43, Iaa10, Iaa23, Iaa95, Ioa95, Iea9, Ifa9, Iaa29, tho-2-IB8a4% ) against harmful plants, such as Polygonum convolvulus galli, when applied by the post-emergence method at an application rate of

288/289

0.32 kg of active substance per hectare.

[989] In this case, for example, compounds ^Nos. IB9aa6, Iaa1, Iaa20, Iaa23, IB9aa1, IB9ba6, IB9aa10, IB9aa23, IB9aa25, IB9aa43 and Iaa10 also show very good activity (80% -100%) against harmful plants, such as Veronica repens, when applied by the post-harvest method emergence at an application rate of 0.32 kg of active substance per hectare.

[990] In this case, for example, compounds ^Nos. Iaa95, Iaa23, IB9aa1, IB9aa10, IB9aa23, IB9aa43, IB9aa25, IB9aa6, Iaa10, Iaa17, Ica83, treo-2IB8aa43 and IA12aa194 also show very good activity (80% 100%) against harmful plants, such as Viola by the post-emergence method at an application rate of 0.32 kg of active substance per hectare.

[991] In this case, for example, compounds ^Nos. Iaa23, IB9aa1, Iaa1, IB9aa23, IB9aa43 and IB9aa25 also show very good activity (80% -100%) against harmful plants, such as Abuthilon theophrasti, when applied by the post-emergence method at an application rate of 0.32 kg of active substance per hectare.

[992] In this case, for example, compounds ^Nos. IB9ba6, IB9aa43, IB9aa6, IB9aa23, IB9aa25, Ifa20, Ica20, Iva2, Ioa2, Iea2, Ica2, treo-2-IB8aa43 and Iva17 also show very good activity (80% -100%) against harmful plants, such as Setaria viridis , when applied by the post-emergence method at an application rate of 0.32 kg of active substance per hectare.

[993] In this case, for example, compounds ^Nos. IB9aa43, IB9aa1, IB9ba6, IB9aa23, IB9aa6, treo-2-IB8aa43 and IB9aa25 also show very good activity (80% -100%) against harmful plants, such as Lolium multiflorum, when applied by the post-emergence method at a rate application rate of 0.32 kg of active substance per hectare.

[994] In this case, for example, compounds ^Nos. IB9aa1, IB9ba6, IB9aa43, IB9aa25, IB9aa6, Iaa95, Iaa23, Ioa95, IB9aa23, Iva1, Iea1, Ica1, Iea20, Ica20, Iva9, Ioa9, Ioa2, Iea2, Iea23, Icao-, I83, I83 2-IB8aa43,

289/289 treo-1-IA12aa49 and IA12aa194 also show very good activity (80% -100%) against harmful plants, such as Echinochloa crus-galli, when applied by the post-emergence method at an application rate of 0, 32 kg of active substance per hectare.

[995] In this case, for example, compounds ^Nos. IB9aa1, IB9ba6, IB9aa43, IB9aa25, IB9aa6, IB9aa10, Iaa95, Iaa23, Ioa95, treo-2-IB8aa43 and IB9aa23 also show very good activity (80% -100%) against harmful plants, such as Avena fatua, when applied by the post-emergence method at an application rate of 0.32 kg of active substance per hectare.

[996] In this case, for example, compounds ^Nos. IB9aa1, IB9ba6, IB9aa43, IB9aa25, Ioa95, treo-2-IB8aa43 and IB9aa23 also show very good activity (80% -100%) against harmful plants, such as Alopecurus myosuroides, when applied by the post-emergence method at a rate application rate of 0.32 kg of active substance per hectare.

[997] In this case, for example, compounds ^Nos. Iaa9, Iea9, Ifa9, Iva2, Ioa2, Iea2, Iaa17, Iva24, Ioa24, Iaa29, Ica29, IA12aa194 and IB10ga6 also show very good activity (80% -100%) against harmful plants, such as Veronica persica, when applied by post-emergence method at an application rate of 0.32 kg of active substance per hectare.

3. Herbicidal action and compatibility with crop plants [998] 3.1 In other tests in the greenhouse, seeds of crop plants were placed in pots on clayey and sandy soil, covered with soil, grown under good growing conditions , it was treated by the pre-emergence method and classified in an analogous way to the harmful plants in section 1. The results show that the compounds according to the invention do not cause any damage in dicot crops, such as soy, cotton, rapeseed, sugar beet and potatoes, when applied by the pre-emergence method, even at high dosages of active compound. In addition, some substances save grass crops, such as barley, wheat, rye, sorghum / millet, corn and rice.

1/27 (I)

Claims (27)

1. Compounds of structural formula (I), or their salts, (R ² ) n characterized in that the symbol L represents a radical of structural formula A ¹ A ² or the symbol A ¹ represents oxygen, sulfur or = NR ^A , the symbol B ¹ represents a radical of structural formulas (B1) to (B14), O R O W IR ¹⁵ W ⁵ ^ R ¹⁶ (B4) Q O R R Q ^{6 /} R ¹⁹ R ²⁰ (B5) (B6) 2/27 (B8) í V ^ R ²⁹ R ³⁰ O ^ R ²⁶ (B9) .29 R Q R (B10) O (B11) O (B12) 32, 'Q (B13) (B14) the symbol A ² represents a radical of structural formulas (A1) to (A12), (A1) O R R R ⁹ ^ W ² ^ Rio (A2) (A3) 3/27 The r13 R, R o ^ w ³ ^ r ¹² (A4) O τ ₇ w R ¹⁹ R ²⁰ (A7) (A8) (A9) O / R r23 ^ \ o or ² '(A10) (A11) (A12) the symbol B ² represents hydroxy, uncle, halogen or a group of formula 5 general OR ³³ , OM, SR ³⁴ , SM or -NRBRC, each of the symbols W ¹ and W ⁶ represents, independently of each other, the divalent oxygen, sulfur group or a group of general formula NH, N- [ (C1-4 alkyl)], C = O (carbonyl), S = O (sulfinyl), SO2 (sulfonyl) or CR ³⁵ R ³⁶ , each of the symbols W ² , W ³ , W ⁴ , W ⁵ and W ⁷ independently represent the divalent oxygen, sulfur group or a group of the general formula NH, N- [(C1 -C4 alkyl)], C = O (carbonyl), S = O (sulfinyl) or SO2 (sulfonyl), each of the symbols Q ¹ , Q ² , Q ³ , Q ⁴ , Q ⁵ , Q ⁶ , Q ⁷ , Q ⁸ and Q ⁹ represent, independently of each other, hydroxy, uncle, halogen or a formula group 15 general OR ³⁷ , SR ³⁸ , SM or OM, 4/27 the symbol M represents an equivalent of a cation, each of the symbols R ^A , R ^B and R ^C independently representing hydrogen, hydroxy, alkoxy (Ci-C4), alkyl (Ci-C4 ), haloalkyl (C1 -C4), phenyl or benzyl, where each of the last two radicals referred to is optionally mono- or poly-substituted with the same or different substituents, or -NR * R **, where each of the symbols R *, R ** independently represents H, alkyl (C1-Ce), alkenyl (C2-C8), alkynyl (C2-Ce), alkoxy (C1-C4) -alkyl (C1-C4) ), alkanoyl (C1-C6) [haloalkyl (C1-C4)] - carbonyl, [alkoxy (C1-C4)] - carbonyl, [haloalkoxy (C1-C4)] - carbonyl, cycloalkyl (C3-C6), cycloalkyl ( C3-C6) -alkyl (C1-C4), phenyl, phenyl-alkyl (C1-C4), where each of these last 4 radicals referred to is unsubstituted in the cycle or is substituted with one or more radicals selected from the group constituted by halogen, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1-C4) and haloalkoxy (C1-C4) or, in the case of cycloalkyl, also with oxo, or the symbols R * and R **, together with the nitrogen atom, represent a 3- to 6-membered heterocycle, which, in addition to the nitrogen atom, may contain plus one or two ring hetero atoms selected from the group consisting of N, O and S and which can be unsubstituted or substituted with one or more radicals selected from the group consisting of alkyl (C-C4), haloalkyl (Ci- C4) and oxo, the symbol (R ⁱ ) m represents m substituents R ⁱ , where the substituent R ⁱ , if m = 1, or each of the substituents R ⁱ , if m is greater than 1, independently of the others, represents halogen, cyano, nitro, hydroxy, alkyl (Ci-Ce), alkenyl (C2-C6), alkynyl (C2-C6), alkoxy (Ci-C8), alkyl (Ci-Ce) -io, alkyl ( Ci-Ce) -sulfinyl, alkyl (Ci-Ce) -sulfonyl, haloalkyl (C1-C6), haloalkoxy (C1-C6), haloalkyl (C1-C6) -thio, haloalkyl (Ci-C6) -sulfinyl, haloalkyl ( C1-6) -sulfonyl, haloalkenyl (C2-C6), haloalkynyl (C2 -C6), alkoxy (C1-C6) -alkyl (C1C), haloalkoxy (C1-C6) -alkyl (C1-C4), cycloalkyl (C3-C6) which is optionally substituted with one or more radicals selected from the set 5/27 by halogen and alkyl (C-C4), cyclolalkoxy (C3-C6) which is optionally substituted with one or more radicals selected from the group consisting of halogen and alkyl (C-C4) or a radical of general formula C ( O) OR ³⁹ , C (O) NR ⁴⁰ R ⁴¹ , C (O) -Het ¹ , NR ⁴² R ⁴³ or Het ² , or where, in each case, two R ² groups located in the ortho position on the ring, in together, they represent a group of the general formula -Z ¹ -A * -Z ² , in which the symbol A * represents an alkylene group having between 1 and 4 carbon atoms and which is optionally substituted with one or more radicals selected from the set consisting of halogen, alkyl (C-C4), haloalkyl (C1-C4), alkoxy (C1-C4) and haloalkoxy (C1-C4), the symbol Z ¹ represents a direct bond, O or S and the symbol Z ² represents a direct bond, O or S, in which the group -Z ¹ -A * -Z ² , together with the carbon atoms, attached to the group of the phenyl ring, form a condensed ring with 5 or 6 members and the symbol (R ² ) n represents n subst ituentes R ² , where the substituent R ² , if n = 1, or each of the substituents R ² , if n is greater than 1, independently of the others, represents halogen, cyano, nitro, hydroxy, (C1) alkyl -Ce), alkenyl (C2-C6), alkynyl (C2-C6), alkoxy (C1-C8), alkyl (C1-Ce) -thio, alkyl (C1-Ce) -sulfinyl, alkyl (C1-Ce) - sulfonyl, halo (C1-C6), haloalkoxy (C1-C6), haloalkyl (C1-C6) -thio, haloalkyl (C1-C6) -sulfinyl, haloalkyl (C1C6) -sulfonyl, haloalkenyl (C2-C6), halo C2-C6), alkoxy (C1-C6) -alkyl (C1C4), haloalkoxy (C1-C6) -alkyl (C1-C4), cycloalkyl (C ₃ -C6) which is optionally substituted with one or more radicals selected from among group consisting of halogen and alkyl (C1-C4), cyclolalkoxy (C ₃ -C6) which is optionally substituted with one or more radicals selected from the group consisting of halogen and alkyl (C1-C4) or a radical of general formula C ( O) OR ⁴⁴ , C (O) NR ⁴⁵ R ⁴⁶ , C (O) -Het ³ , NR ⁴⁷ R ⁴⁸ or Het ⁴ , or where, in each case, two local R ² groups in the ortho position in the 6/27 ring together represent a group of the general formula -Z ³ -A ** - Z ⁴ , in which the symbol A ** represents an alkylene group having between 1 and 4 carbon atoms and which is optionally substituted with one or more radicals selected from the group consisting of halogen, alkyl (Ci-C4), haloalkyl (Ci-C4), alkoxy (Ci-C4) and haloalkoxy (Ci-C4), the symbol Z ³ represents a direct bond, O or S and the symbol Z ⁴ represents a direct bond, O or S, in which the group -Z ³ -A ** - Z ⁴ , together with the carbon atoms, attached to the phenyl ring group, form a ring condensed with 5 or 6 members, each of the symbols R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ independently represent hydrogen, halogen, cyano, nitro, hydroxy, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1 -C4), halo (C1-C4) alkoxy (C1-C4) -alkyl (C1-C4), haloalkoxy (C1-C4) alkyl (C1-C4), cycloalkyl (C3-C6), h alocycloalkyl (C3-C6), cycloalkoxy (C3-C6), alkenyl (C2-C6), haloalkenyl (C2-C6), alkynyl (C2-C6), haloalkynyl (C2-C6), alkyl (C1-C4) -io , (C1-C4) alkylsulfonyl, (C1-C4) alkylsulfinyl, phenyl which is optionally substituted or a C (O) OR ⁴⁹ , C (O) NR ⁵⁰ R ⁵¹ , C (O) Het ^{5 group} , NR ⁵² R ⁵³ or Het ⁶ or the symbols R ³ and R ⁵ , in the group of structural formula (B1) or (A1), together, represent a divalent bridge of a straight chain alkylene or alkenylene group that has 2 or 3 carbon atoms, where a CH2 group in the chain can also be replaced by an oxygen atom and where a CH2 group or a CH group in the chain is optionally substituted with one or more radicals selected from the group consisting of (C1-) alkyl C4), haloalkyl (C1-C4), alkoxy (C1-C4) and haloalkoxy (C1-C4), the symbol R ²¹ represents hydrogen, alkyl (C1-C4), haloalkyl (C1-C4), cycloalkyl (C3-C6) ), halocycloalkyl (C3-C6) or a group C (O) OR ⁵⁴ , C (O) NR ⁵⁵ R ⁵⁶ , C (O) Het ⁷ , NR ⁵⁷ R ⁵⁸ o u Het ⁸ , the symbol R ²² represents hydrogen, (C1-C4) alkyl, haloalkyl (C1-C4), 7/27 cycloalkyl (C3-C6), halocycloalkyl (C3-C6), alkyl (C1-C4) -thio, alkyl (C1-C4) sulfonyl, alkyl (C1-C4) -sulfinyl or a group of general formula C ( O) OR ⁵⁹ , C (O) NR ⁶⁰ R ⁶¹ , C (O) Het ⁹ , NR ⁶² R ⁶³ or Het ¹⁰ , each of the symbols R ²³ and R ²⁹ independently representing hydrogen, alkyl (C1-C4), haloalkyl (C-C4), cycloalkyl (C3-C6), halocycloalkyl (C3-C6), alkoxy (C1-C4) or haloalkoxy (C1-C4), each of the symbols R ²⁴ and R ³⁰ independently represent hydrogen, halogen, cyano, alkyl (C1-C4), haloalkyl (C1-C4), cycloalkyl (C3-C6), halocycloalkyl (C3-C6), alkoxy (C-C4) or haloalkoxy (C1-C4), each of the symbols R ²⁵ , R ²⁶ , R ³ⁱ and R ³² independently represent hydrogen, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1C ), halo (C1-C4), alkoxy (C1-C4) -alkyl (C1-C4), haloalkoxy (C1-C4) -alkyl (C1C), cycloalkyl (C3-C6), halocycloalkyl (C3-C6), cycloalkoxy (C3-C6), alkenyl (C2C6), haloalkenyl (C2-C6), alk inyl (C2-C6), haloalkynyl (C2-C6), (C1-C4) alkylthio, (C1-C4) alkylsulfonyl, (C1-C4) alkylsulfinyl, NR ⁶⁴ R ⁶⁵ or Het ⁱⁱ , o symbol R ²⁷ represents hydrogen, alkyl (C-C6), haloalkyl (C-C4), cycloalkyl (C3-C6) or halocycloalkyl (C3-C6), symbol R ²⁸ represents hydrogen, alkyl (C-C6), haloalkyl ( Ci-C4) or a radical of the general formula C (O) OR ⁶⁶ , each of the symbols R ³³ , R ³⁴ , R ³⁷ and R ³⁸ independently representing alkyl (Ci-C8), cycloalkyl ( C3-C6), phenyl, in which each of these three referred radicals, in each case and independently of each other, is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, cyan, nitro , hydroxy, (C1 -C4) alkoxy, (C1-C4) alkylthio, and, in the case of a cycloalkyl or phenyl radical as the original radical, also with (C1-C4) alkyl and halo (C1-C4) alkyl, or a group of general formula -C (O) R ⁶⁷ , -C (O) OR ⁶⁸ , -C (O) NR ⁶⁹ R ⁷⁰ , -C (O) Het ^{i 2} or -SO2R ^{7 1} , each of the symbols R ³⁵ and R ^{36 has} , independently of each other, the meaning defined for the symbol R ³ , each of the symbols R ³⁹ , R ⁴⁴ , R ⁴⁹ , R ⁵⁴ , R ⁵⁹ and R ⁶⁶ represent, in a 8/27 independently of each other, hydrogen, alkyl (C-C4), haloalkyl (C-C4), cycloalkyl (C3-C6), halocycloalkyl (C3-C6), alkenyl (C2-C4), haloalkenyl (C2-C4) ), alkynyl (C2-C4) or the mentioned group M, each of the symbols R ⁴⁰ , R ⁴¹ , R ⁴² , R ⁴³ , R ⁴⁵ , R ⁴⁶ , R ⁴⁷ , R ⁴⁸ , R ⁵⁰ , R ⁵¹ , R ⁵² , R ⁵³ , R ⁵⁵ , R ⁵⁶ , R ⁵⁷ , R ⁵⁸ , R ⁶⁰ , R ⁶¹ , R ⁶² , R ⁶³ , R ⁶⁴ , R ⁶⁵ , R ⁶⁹ and R ⁷⁰ represent, independently of each other, hydrogen, alkyl (C-C6), alkenyl (C2-C6) or alkynyl (C2-C6), where each of the last 3 radicals referred to, in each case and independently of the others, is unsubstituted or is substituted with a or more radicals selected from the group consisting of halogen, nitro, cyano and phenyl, which is optionally substituted, or cycloalkyl (C3-C6) or phenyl, in which each of the last 2 radicals mentioned, in each case and in a different way independent of the other, it is unsubstituted or is substituted with one or more radicals selected between the group consisting of halogen, nitro, cyano, alkyl (C1-C4), haloalkyl (C1-C4), phenyl or benzyl, in which each of the last 2 radicals referred to is optionally substituted, the symbol R ⁶⁷ represents hydrogen, alkyl (C1 -C8) or haloalkyl (C1-C8), where each of the last 2 radicals referred to, independently of the other, is optionally interrupted in the alkyl group with oxygen or sulfur, or phenyl or benzyl, where each one of these last 2 radicals, independently of each other, is unsubstituted or is substituted with one or more radicals selected from the group consisting of halogen, cyano, alkyl (C-C4), alkenyl (C2-C4), alkynyl ( C2-C4), cycloalkyl (C3-C6), haloalkyl (C1-C4) and halocycloalkyl (C3-C6), the symbol R ⁶⁸ represents alkyl (C1-C8), haloalkyl (C1-C8), cycloalkyl (C3-C6) ), halocycloalkyl (C3-C6), alkenyl (C2-C8), haloalkenyl (C2-C8) or alkynyl (C2-C4), the symbol R ⁷ⁱ represents alkyl (C-C6), haloalkyl (C1-C6) or phenyl or benzyl, where each of these last 2 radicals, independently of each other, is unsubstituted or is substituted with one or more selected radicals 9/27 between the set consisting of halogen, cyano, alkyl (C-C4), alkenyl (C2-C4), alkynyl (C2-C4), cycloalkyl (C ₃ -C6), haloalkyl (Ci-C4) and halocycloalkyl ( C ₃ -C6), each of the symbols Het ¹ , Het ² , Het ³ , Het ⁴ , Het ⁵ , Het ⁶ , Het ⁷ , Het ⁸ , Het ⁹ , Het ¹⁰ , Het ¹¹ and Het ¹² independent of each other, a saturated or partially unsaturated radical of a heterocycle that has 3 to 9 ring atoms and at least one nitrogen atom as the ring heteroatom at position 1 of the ring and, optionally, 1, 2 or 3 other ring hetero atoms of the set consisting of N, O and S, in which the radical of the heterocycle is attached by the nitrogen atom at position 1 of the ring to the remainder of the molecule of the compound of formula (I) and in which the heterocycle is unsubstituted or is substituted with one or more radicals selected from the group consisting of halogen, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1-C4), haloalkox i (C1C4), (C1 -C4) alkyl and thio and oxo, and each of the symbols m and n independently represent 0, 1, 2, 3, 4 or 5. Compounds or their salts according to claim 1, characterized in that the symbol (R ¹ ) m represents m substituents R ¹ , where the substituent R ¹ , if m = 1, or each of the substituents R ¹ , if m is greater than 1, they independently represent halogen, cyano, nitro, hydroxy, alkyl (C1-C6), alkenyl (C2-C4), alkynyl (C2-C4), alkoxy (C1-C6 ), (C1-C6) alkylthio, (C1-C6) alkylsulfinyl, (C1-C6) alkylsulfonyl, halo (C1-C4) haloalkyl (C1-C4), haloalkyl (C1-C4) - thio, halo (C1-C4) -sulfinyl, haloalkyl (C1C4) -sulfonyl, haloalkenyl (C2-C4), haloalkynyl (C2-C4), alkoxy (C1-C4) -alkyl (C1C4), haloalkoxy (C1-C4) -alkyl (C1-C4), cycloalkyl (C3-C6) which is optionally substituted with one or more radicals selected from the group consisting of halogen and alkyl (C1-C4), cyclolalkoxy (C3-C6) which is optionally substituted with a or more radicals selected from the group consisting of halogen and (C1-C4) alkyl or a radical of general formula C (O) OR ³⁹ , 10/27 C (O) NR ⁴⁰ R ⁴¹ , C (O) -Het ¹ , NR ⁴² R ⁴³ or Het ² , or where, in each case, two R ² groups, located in the ortho position on the ring, together, represent a group of general formula -Z ¹ -A * -Z ² , in which the symbol A * represents an alkylene group having between 1 and 4 carbon atoms and which is optionally substituted with one or more radicals selected from the group consisting of halogen , alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1-C4) and haloalkoxy (C1-C4), the symbol Z ¹ represents a direct bond, O or S and the symbol Z ² represents a direct bond , O or S, in which the group -Z ¹ -A * -Z ² , together with the carbon atoms, attached to the group, of the phenyl ring, form a condensed ring with 5 or 6 members and the symbol R ³⁹ represents hydrogen, alkyl (C1-C4), haloalkyl (C1-C4), cycloalkyl (C3-C6), halocycloalkyl (C3-C6), alkenyl (C2-C4), haloalkenyl (C2-C4), alkynyl (C2-C4) or the equivalent of a cation, each of the symbols R ⁴⁰ , R ⁴¹ , R ⁴² , R ⁴³ represents, independently, hydrogen or alkyl (C1-C4) which is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, nitro, cyano and phenyl, or represent cycloalkyl (C3-C6) or phenyl, in which each of the last 2 radicals referred to, independently of each other, is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, alkyl (C1-C4), haloalkyl (C1-C4 ), phenyl or benzyl, each of the symbols Het ¹ and Het ² independently represent a saturated or partially unsaturated radical of a heterocycle that has 3 to 6 ring atoms and at least one nitrogen atom as a hetero atom of the ring in position 1 of the ring and, optionally, 1,2 or 3 other ring heteroatoms of the set consisting of N, O and S, where the radical of the heterocycle is linked by the nitrogen atom in position 1 of the ring to the remainder of the form compound molecule structural formula (I) and where the 11/27 heterocycle is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, alkyl (C-C4), haloalkyl (C-C4) and oxo, and the symbol m represents 0, 1, 2, 3, 4 or 5. Compounds, or their salts, according to claim 1 or 2, characterized in that the symbol (R ² ) n represents n substituents R ² , wherein the substituent R ² , if n = 1, or each of the substituents R ² , if not greater than 1, independently represent halogen, cyano, nitro, hydroxy, alkyl (Ci-Ce), alkenyl (C2-C4), alkynyl (C2-C4), alkoxy (Ci -C6), (C1-C) alkylthio, (C1-C6) alkylsulfinyl, (C1-C6) alkylsulfonyl, halo (C1-C4) haloalkyl (C1-C4), haloalkyl (C1-C4) ) -thio, halo (C1-C4) -sulfinyl, haloalkyl (C1-C4) -sulfonyl, haloalkenyl (C2-C4), haloalkynyl (C2-C4), alkoxy (C1-C4) -alkyl (CiC4), haloalkoxy (Ci- C4) -alkyl (C1-C4), cycloalkyl (C3-C6) which is optionally substituted with one or more radicals selected from the group consisting of halogen and alkyl (C1-C4), cyclolalkoxy (C3-C6) which is optionally substituted with one or more radicals selected from the group consisting of halogen and alkyl (C1-C4) or a radical of formula the general C (O) OR ⁴⁴ , C (O) NR ⁴⁵ R ⁴⁶ , C (O) -Het ³ , NR ⁴⁷ R ⁴⁸ or Het ⁴ , or in which, in each case, two R ² groups, located in the ortho in the ring, together, represent a group of general formula -Z ³ -A * -Z ³ , where A ** represents an alkylene group that has between 1 and 4 carbon atoms and that is optionally substituted with one or more radicals selected from the group consisting of halogen, alkyl (C-C4), haloalkyl (C-C4), alkoxy ( Ci-C4) and haloalkoxy (Ci-C4), the symbol Z ³ represents a direct bond, O or S and the symbol Z ⁴ represents a direct bond, O or S, where the group -Z ³ -A * -Z ⁴ , together with the carbon atoms, attached to the group, of the phenyl ring, form a condensed ring with 5 or 6 members and 12/27 the symbol R ⁴⁴ represents hydrogen, alkyl (C-C4), haloalkyl (C-C4), cycloalkyl (C3-C6), halocycloalkyl (C3-C6), alkenyl (C2-C4), haloalkenyl (C2-C4) ), alkynyl (C2-C4) or the equivalent of a cation, each of the symbols R ⁴⁵ , R ⁴⁶ , R ⁴⁷ and R ⁴⁸ independently represent hydrogen or alkyl (C-C4) which is not substituted or substituted with one or more radicals selected from the group consisting of halogen, nitro, cyano and phenyl, or represent cycloalkyl (C3-C6) or phenyl, in which each of the last 2 radicals referred to, in each case in a different way independent of each other, it is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, alkyl (C-C4), haloalkyl (C1-C4), phenyl or benzyl, each of the symbols Het ³ and Het ⁴ represent, independently of each other, a saturated or partially unsaturated radical of a heterocycle that has 3 to 6 ring atoms and at least enos a nitrogen atom as a ring hetero atom at position 1 of the ring and, optionally, 1,2 or 3 other ring hetero atoms of the set consisting of N, O and S, where the radical of the heterocycle is linked by the nitrogen atom in position 1 of the ring to the remaining part of the compound of the compound of structural formula (I) and in which the heterocycle is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, (C-C4) alkyl, haloalkyl ( C1-C4) and oxo and the symbol n represents 0, 1, 2, 3, 4 or 5. Compounds or their salts according to any one of claims 1 to 3, characterized in that the symbol (R ⁱ ) m represents m substituents R ⁱ , in which the substituent R ⁱ , if m = 1, or each of the substituents R ⁱ , if m is greater than 1, independently of one another, represent halogen, cyano, nitro, hydroxy, (C1-C4) alkyl, (C1-C4) alkoxy, (C1-C4) alkyl, thio, (C1-C4) alkylsulfinyl, (C1-C4) alkylsulfonyl, halo (C1-C4) haloalkyl (C1-C4), haloalkyl (C1-C4) -thio, haloalkyl (C1-C4) -sulfinyl, haloalkyl (C1-C4) -sulfonyl, 13/27 alkoxy (C1-C4) -alkyl (C1-C4), cycloalkyl (C3-C6) or a radical of the general formula C (O) OR ³⁹ , C (O) NR ⁴⁰ R ⁴¹ , C (O) - Het ¹ , NR ⁴² R ⁴³ or Het ² , or in which, in each case, two R ¹ groups, located in the ortho position on the ring, together represent a group of general formula -Z ¹ -A * -Z ² , on what A * represents an alkylene group that has between 1 and 4 carbon atoms and that is optionally substituted with one or more radicals selected from the group consisting of halogen, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1 -C4) and haloalkoxy (C1-C4), the symbol Z ¹ represents a direct bond, O or S and the symbol Z ² represents a direct bond, O or S, where the group -Z ¹ -A * -Z ² , together with the carbon atoms, linked to the group, of the phenyl ring, form a condensed ring with 5 or 6 members and the symbol R ³⁹ represents hydrogen, (C1-C4) alkyl or the equivalent of a cation, each of symbols R ⁴⁰ , R ⁴¹ , R ⁴² and R ⁴³ independently represent hydrogen, alkyl (C1-C4), haloalkyl (C1-C4), benzyl, cycloalkyl (C3-C6) or phenyl and, in in particular, hydrogen, methyl or ethyl, each of the symbols Het ¹ and Het ² independently represent a morpholino, piperidine or pyrrolidine group, the symbol m re whether 0, 1, 2, 3, 4 or 5, the symbol (R ² ) does not represent n substituents R ² , where the substituent R ² , if n = 1, or each of the substituents R ² , if n is greater than to 1, independently of one another, represents halogen, cyano, nitro, hydroxy, (C1-C4) alkyl, (C1-C4) alkoxy, (C1-C4) alkyl, thio, (C1-C4) sulfinyl alkyl, (C1-C4) alkylsulfonyl, halo (C1-C4) haloalkoxy (C1-C4), haloalkyl (C1-C4) -thio, haloalkyl (C1-C4) -sulfinyl, halo (C1-C4) -sulfonyl, alkoxy (C1-C4) -alkyl (C1-C4), cycloalkyl (C3-C6) or a radical of the general formula C (O) OR ⁴⁴ , C (O) NR ⁴⁵ R ⁴⁶ , C (O) -Het ³ , NR ⁴⁷ R ⁴⁸ or Het ⁴ , or where, in each case, two R ² groups, located in the ortho position in the 14/27 ring together represent a group of general formula -Z ³ -A ** - Z ⁴ , where A ** represents an alkylene group that has between 1 and 4 carbon atoms and that is optionally substituted with one or more radicals selected from the group consisting of halogen, alkyl (C-C4), haloalkyl (C-C4), alkoxy ( Ci-C4) and haloalkoxy (Ci-C4), the symbol Z ³ represents a direct bond, O or S and the symbol Z ⁴ represents a direct bond, O or S, where the group -Z ³ -A ** - Z ⁴ , together with the carbon atoms, linked to the group, of the phenyl ring, form a condensed ring with 5 or 6 members and the symbol R ⁴⁴ represents hydrogen, (C 1 -C 4) alkyl or the equivalent of a cation, each one of the symbols R ⁴⁵ , R ⁴⁶ , R ⁴⁷ and R ⁴⁸ independently represents hydrogen, alkyl (C-C4), haloalkyl (C-C4), benzyl, cycloalkyl (C3-C6) or phenyl, each of the symbols Het ³ and Het ⁴ independently represents a morpholino, piperidine or pyrrolidine group and the symbol n represents 0, 1, 2, 3, 4 or 5. Compounds or their salts according to any one of claims 1 to 4, characterized in that the symbol L represents a radical of structural formula A ¹ B ¹ in which the symbols A ⁱ and B ⁱ have the meanings defined for the structural formula (I). 6. Compounds or their salts according to claim 5, characterized in that the symbol A ⁱ represents oxygen, sulfur or = NR ^A , the symbol B ⁱ represents a radical of the structural formulas (B1) to (B14) 15/27 mentioned, the symbol R ^A represents hydrogen, hydroxy, alkoxy (C1-C4), alkyl (C1-C4), haloalkyl (C1-C4), phenyl which is unsubstituted or substituted with one or more radicals selected from among the group consisting of halogen, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1-C4), haloalkoxy (C1-C4), or benzyl which is unsubstituted in the phenyl group or is substituted with one or more radicals selected from the group consisting of halogen, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1-C4), haloalkoxy (C1-C4), or -NR * R **, where each of symbols R *, R ** independently represents H, alkyl (C-C4), alkenyl (C2-C4), alkynyl (C2-C4), alkoxy (C-C4) -alkyl (Ci- C4), alkanoyl (C1-C4), [haloalkyl (C1-C4)] - carbonyl, [alkoxy (C1-C4)] - carbonyl, [haloalkoxy (C1-C4)] - carbonyl, cycloalkyl (C3-C6), cycloalkyl (C3-Ce) -alkyl (C1C4), phenyl, phenyl-alkyl (C1-C4), where each of the last 4 radicals referred to is unsubstituted in the cycle or is substituted with one or more radicals selected from the group consisting of halogen, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1-C4) or haloalkoxy (C1-C4) or, in the case of cycloalkyl, also with oxo or the symbols R * and R **, together with the nitrogen atom, represent a 3- to 6-membered heterocycle, which, in addition to the nitrogen atom, can contain one or two more hetero atoms in the ring selected from the group consisting of N, O and S and which can be unsubstituted or can be substituted with one or more radicals selected from the group consisting of alkyl (C1-C4), haloalkyl (C1-C4) and oxo, the symbols (R ⁱ ) m, (R ² ) n, R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ⁱ⁰ , R, R ⁱ² , R ⁱ³ , R ⁱ⁴ , R ⁱ⁵ , R ⁱ⁶ , R ⁱ⁷ , R ⁱ⁸ , R ⁱ⁹ , R ²⁰ , R ^{2 1} , R ²² , R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ , R ²⁸ , R ²⁹ , R ³⁰ , R ^{3 1} e R ³² have the meanings mentioned above, each of the symbols W ⁱ and W ⁶ represents, independently of each other, the divalent oxygen, sulfur group or a group of the general formula NH, N- [(C-C4) alkyl] , C = O, S = O, SO2 or CR ³⁵ R ³⁶ , each of the symbols W ² , W ³ , W ⁴ , W ⁵ and W ⁷ represents, in a different way 16/27 independent of each other, the divalent group of general formula O, S, NH, N- [(C 1 -C4 alkyl)], C = O, S = O or SO2, each of the symbols Q1, Q2, Q3, Q4 , Q5, Q6, Q7, Q8 and Q9 independently represent hydroxy, uncle, halogen or a group of general formula OR ³⁷ , SR ³⁸ , SM or OM, the symbol M represents the equivalent of a cation, each of the symbols R ³⁵ and R ^{36 has} , independently of each other, the meaning defined for the symbol R ³ or, preferably, independently represents H, alkyl (C-C4) or haloalkyl (C1-C4), preferably H or (C1-C2) alkyl, and in particular H, methyl or ethyl and the symbols R ³⁷ , R ³⁸ , R ⁶⁶ , R ⁶⁷ , R ⁶⁸ , R ⁶⁹ , R ⁷⁰ , R ⁷¹ , Het ¹² and M have the meanings mentioned before. Compounds or their salts according to claim 5 or 6, characterized in that each of the symbols R ³⁷ and R ³⁸ independently represents alkyl (C 1 -C 6), haloalkyl (C 1 -C 6) , (C1-C4) alkoxy (C1-C4), cycloalkyl (C3-C6) which is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, alkyl (C-C4) and alkoxy ( (C1-C4), phenyl which is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, cyano, hydroxy, nitro, alkyl (C1-C4), haloalkyl (C1-C4) and alkoxy (C1- C4), or a group of general formula -C (O) R ⁶⁷ , -C (O) OR ⁶⁸ , -C (O) NR ⁶⁹ R ⁷⁰ , -C (O) Het ⁱ² or -SO2RU the symbol R ⁶⁷ represents hydrogen, alkyl (C1-C6), haloalkyl (C1-C4), phenyl or benzyl, in which each of these last 2 radicals, independently of each other, is unsubstituted or substituted with one or more radicals selected from among group consisting of halogen, cyan, alkyl ( Ci-C4) and haloalkyl (Ci-C4), the symbol R ⁶⁸ represents alkyl (Ci-C6) or haloalkyl (Ci-C4), each of the symbols R ⁶⁹ and R ⁷⁰ independently represents hydrogen , (C-C4) alkyl, benzyl, (C3-C6) cycloalkyl or phenyl, where 17/27 each of these last 2 radicals, independently of each other, is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, nitro, cyano, alkyl (Ci-C4) and haloalkyl (CiC4 ), the symbol R ⁷¹ represents alkyl (C1-C4), haloalkyl (C1-C4), phenyl or benzyl, in which each of these last 2 radicals, independently of each other, is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, cyano, (C-C4) alkyl, alkenyl (C2-C4) and (C2-C4) -haloalkyl, the symbol Het ⁱ² represents a saturated or partially unsaturated radical of a heterocycle that has 3 to 6 ring atoms and at least one nitrogen atom as the ring heteroatom at position 1 of the ring and, optionally, 1, 2 or 3 other ring hetero atoms of the set consisting of N, O and S, where the radical of heterocycle on the nitrogen atom at position 1 of the ring is attached to the remaining part of the molecule d the compound of structural formula (I) and in which the heterocycle is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1-4) C4), haloalkoxy (C1-C4), alkyl (C1-C4) thio and oxo and the symbol M represents an equivalent to a metal ion, an ammonium ion that is optionally substituted with 1 to 4 radicals, the same or different, selected among the group consisting of alkyl (C1-C4), cycloalkyl (C3-C6), phenyl, cycloalkyl (C3-C6) -alkyl (C1-C4) and phenyl-alkyl (C1-C4), or a tertiary sulfonium ion that is substituted with 3 radicals, the same or different, selected from the group consisting of alkyl (C1-C4), cycloalkyl (C3-C6), phenyl, cycloalkyl (C3-C6) -alkyl (Ci-C4) and phenyl-alkyl (Ci -C4). Compounds or their salts according to any one of claims 1 to 7, characterized in that the symbol L represents a radical of structural formula 18/27 B ² where the symbols A ² and B ² have the meanings mentioned. Compounds or their salts according to claim 8, characterized in that the symbol A ² represents a radical of the structural formulas (A1) to (A12) mentioned, the symbol B ² represents hydroxy, uncle, halogen or a group of general formula OR ³³ , OM, SR ³⁴ , SM or -NR ^B R ^C , the symbols R ^B and R ^C independently represent hydrogen, hydroxy, alkoxy (C1-C4), alkyl (C1-C4 ), haloalkyl (C1-C4), phenyl which is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1C), haloalkoxy (Ci-C4), or benzyl that is unsubstituted in the phenyl group or that is substituted with one or more radicals selected from the group consisting of halogen, alkyl (Ci-C4), haloalkyl (Ci-C4), alkoxy (Ci- C4), haloalkoxy (C1C4), or -NR * R **, where each of the symbols R *, R ** independently represents H, alkyl (C1-C4), alkenyl (C2-) C4), alkynyl (C2-C4), alkoxy (Ci -C4) -alkyl (C1-C4), alkanoyl (C1-C4), [haloalkyl (C1-C4)] - carbonyl, [alkoxy (C1-C4)] - carbonyl, [haloalkoxy (C1-C4)] - carbonyl , cycloalkyl (C3-C6), cycloalkyl (C3-Ce) -alkyl (C1-C4), phenyl, phenyl-alkyl (C1-C4), where each of the last 4 radicals referred to is unsubstituted in the cycle or is substituted with one or more radicals selected from the group consisting of halogen, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1-C4) or haloalkoxy (C1-C4) or, in the case of cycloalkyl, also with oxo or the symbols R * and R **, together with the nitrogen atom, represent a 3- to 6-membered and preferably saturated heterocycle, which, in addition to the nitrogen atom, may contain one or two more hetero atoms in the ring selected from the set consisting of N, O and S, and 19/27 which can be unsubstituted or can be substituted with one or more radicals selected from the group consisting of alkyl (C-C4), haloalkyl (C-C4) and oxo, the symbols (R ¹ ) m, (R ² ) n, R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ and R ²⁶ have the meanings mentioned above, each of the symbols W ¹ and W ⁶ represents, independently of each other, the group divalent oxygen, sulfur or a group of the general formula NH, N- [(C1-C4 alkyl)], C = O, S = O, SO2 or CR ³⁵ R ³⁶ , each of the symbols W ² , W ³ , W ⁴ , W ⁵ and W ⁷ represent, independently of each other, the divalent group of general formula O, S, NH, N- [(C1 C4 alkyl)], C = O, S = O or SO2, each of symbols R ³³ and R ³⁴ independently represent (C1-C4) alkyl, haloalkyl (C1-C4), alkoxy (C1-C4) -alkyl (C1-C4), cycloalkyl (C3-C6) which is unsubstituted or is replaced with one or more ra dicals selected from the group consisting of halogen, alkyl (C1-C4) and alkoxy (C1-C4), phenyl which is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, cyano, hydroxy, nitro, alkyl (C1-C4), haloalkyl (C1-C4) and alkoxy (C1-C4), or a group of general formula -C (O) R ⁶⁷ , -C (O) OR ⁶⁸ , -C (O) NR ⁶⁹ R ⁷⁰ , -C (O) Het ¹² or -SO2R ⁷¹ , each of the symbols R ³⁵ and R ^{36 has} , independently of each other, the meaning defined for the symbol R ³ , the symbol R ⁶⁷ represents hydrogen, alkyl (C1-C6), haloalkyl (C1-C4), phenyl or benzyl, in which each of these last 2 radicals, independently of each other, is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, cyano, alkyl (C1-C4) and haloalkyl (C1-C4) and, in particular, H or alkyl (C1-C4), the symbol R ⁶⁸ represents alkyl (C1-C6) or haloalkyl (C1-C4) and , in particular, alkyl (C1-C4), each of the symbols the R ⁶⁹ and R ⁷⁰ represent, independently 20/27 with each other, hydrogen, alkyl (C-C4), benzyl, cycloalkyl (C3-C6) or phenyl, in which each of these last 2 radicals, independently of each other, is unsubstituted or substituted with a or more radicals selected from the group consisting of halogen, nitro, cyano, alkyl (Ci-C4) and haloalkyl (CiC4) and, in particular, each of them independently represent H or alkyl (Ci-Ce ), the symbol R ⁷¹ represents alkyl (C-C4), haloalkyl (C-C4), phenyl or benzyl, in which each of these last 2 radicals, independently of each other, is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, cyano, alkyl (C-C4), alkenyl (C2-C4) and haloalkyl (C1-C4) and, in particular, alkyl (C1-C4), haloalkyl (C1-C4) , benzyl or phenyl that is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, (C1-C4) alkyl and haloalk uila (Ci-C4), the symbol Het ⁱ² represents a saturated or partially unsaturated radical of a heterocycle that has 3 to 6 ring atoms and at least one nitrogen atom as the ring hetero atom at position 1 of the ring and, optionally, 1 , 2 or 3 other ring hetero atoms of the set consisting of N, O and S, where the radical of the heterocycle in the nitrogen atom at position 1 of the ring is attached to the remainder of the molecule of the compound of formula (I) and in that the heterocycle is unsubstituted or substituted with one or more radicals selected from the group consisting of halogen, alkyl (C1-C4), haloalkyl (C1-C4), alkoxy (C1-C4), haloalkoxy (C1-C4), (C 1 -C 4) alkyl thio and oxo. Compounds, or their salts, according to any one of claims 1 to 9, characterized in that the compound is present in the form of an enriched racemate. Compounds, or their salts, according to any one of claims 1 to 9, characterized in that the compound is present in the form of an enriched treo-2 enantiomer that has the stereochemical configuration 21/27 [2R, 3R]. Process for the preparation of a compound of formula (I) according to any one of claims 1 to 11, or a salt thereof, characterized by (a) for preparing the compounds of formula (I), and their salts, in which the symbol L represents a radical of structural formula C (= A ¹ ) -B ¹ , the symbol B ¹ represents a radical of structural formulas (B1) to (B9) and (B11) to (B14) and each of the symbols Q ¹ to Q ⁹ represents OH, SH, SM or OM and the other radicals have the meanings defined in the respective compound of structural formula (I) to be prepared, if a compound of structural formula (II) is reacted wherein the symbols A ¹ , (R ¹ ) m and (R ² ) n have the meanings defined in structural formula (I) and Y represents a leaving group, preferably a halogen atom, and in particular a chlorine atom, directly with a compound of general formula HB ¹ , in which the symbol B ¹ has the meaning defined in the radical L and each of the symbols Q ¹ to Q ⁹ has the meaning defined in the compound of structural formula (I) to be prepared, to obtain the compound (I), or to obtain the O- or S-alkylation product, as an intermediate, and submit rearrangement of the O- or S-alkylation intermediate formed to obtain the compound of structural formula (I), as a C-alkylation product or (b) to prepare the compounds of structural formula (I), and their salts, where the symbol L represents a radical of structural formula -C (= A ¹ ) -B ¹ , the symbol B ¹ represents a radical of structural formulas (B1) to (B7) and (B11) to (B14) and each of the symbols Q ¹ to Q ⁹ , in group B ¹ , represents a group of 22/27 general formula SH or SM and the other radicals have the meanings defined in the respective compound of structural formula (I) to be prepared, by reacting a compound of structural formula (I), in which the symbol L represents a radical of structural formula -C (= A ¹ ) -B ¹ , where the symbol A ¹ has the meaning defined in the structural formula (I) and the symbol B ¹ has the meaning defined in a manner analogous to the radical B ¹ in the structural formula (I), with the difference of each of the symbols Q ¹ to Q ⁹ , in group B ¹ , represent the group OH or OM, with a halogenating agent to obtain the compound (I), in which each of the symbols Q ¹ to Q ⁹ , in group B ¹ , represents a halogen atom, and to be reacted with a sulfurizing agent and optionally separate the desired compound of structural formula (I) from the reaction mixture or to isolate, or (c) to prepare the compounds of structural formula (I), and their salts, in which the sy symbol L represents a radical of the general formula -C (= A ¹ ) -B ¹ , the symbol B ¹ represents a radical of structural formulas (B1) to (B7) and (B11) to (B14) and each of the symbols Q ¹ to Q ⁹ , in group B ¹ , represents a group of general formula OR ³⁷ and the other radicals have the meanings defined in the respective compound of structural formula (I) to be prepared, by reacting a compound of structural formula (I ), where the symbol L represents a radical of the general formula -C (= A ¹ ) -B ¹ , where the symbol A ¹ has the meaning defined in structural formula (I) and the symbol B ¹ has the defined meaning of a mode analogous to the radical B ¹ in structural formula (I), with the exception of each of the symbols Q ¹ to Q ⁹ , in the group B ¹ , represent the group OH or OM, with a compound of the general formula Y'-R ³⁷ , in which the symbol Y 'represents a leaving group and the symbol R ³⁷ has the meaning defined in structural formula (I), and is optionally separated te the desired compound of structural formula (I) from the reaction mixture or isolate or (d) to prepare the compounds of structural formula (I), and their salts, in which L represents a radical of structural formula -C (= A ¹ ) -B ¹ , the symbol B ¹ represents a radical of structural formulas (B1) to (B7) and (B11) a 23/27 (B14) and each of the symbols Q ¹ to Q ⁹ , in group B ¹ , represents a group of general formula SR ³⁸ and the other radicals have the meanings defined in the respective compound of structural formula (I) that is intended prepare, react a compound of structural formula (I), in which the symbol L represents a radical of structural formula -C (= A ¹ ) -B ¹ , in which the symbol A ¹ has the meaning defined in the structural formula ( I) and the symbol B ¹ has the meaning defined in an analogous way to the radical B ¹ in structural formula (I), with the difference of each of the symbols Q ¹ to Q ⁹ , in group B ¹ , representing the group SH or SM, with a compound of the general formula Y'-R ³⁸ , in which the symbol Y 'represents a leaving group and the symbol R ³⁸ has the meaning defined in the structural formula (I), and the desired compound of the structural formula is optionally separated (I) from the reaction mixture or isolate or (e) to prepare the compounds of f Structural Formula (I) and salts thereof, wherein L is a radical of formula -C (= A ¹⁾ -B ^1, the symbol B ¹ is a radical of formulas (B1) to (B7) and (B11) to (B14) and each of the symbols Q ¹ to Q ⁹ , in group B ¹ , represents a group of general formula SR ³⁸ and the other radicals have the meanings defined in the respective compound of structural formula (I) that are intends to prepare, to react a compound of structural formula (I), in which the symbol L represents a radical of structural formula -C (= A ¹ ) -B ¹ , in which the symbol A ¹ has the meaning defined in the structural formula (I) and the symbol B ¹ has the meaning defined in an analogous way to the radical B ¹ in structural formula (I), with the difference of each of the symbols Q ¹ to Q ⁹ , in the group B ¹ , representing an atom of halogen, with a thio compound of general formula HSR ³⁸ and optionally separate the desired compound of structural formula (I) from the reaction mixture or isolate or (f) to prepare the compounds of structural formula (I), and their salts, in which L represents a radical of structural formula -C (= A ¹ ) -B ¹ and the symbol B ¹ represents a group of structural formula (B10) [= compound (I-B10)], if a compound of structural formula (I) is reacted, in which the symbol L 24/27 represents a radical of structural formula -C (= A ¹ ) -B *, the symbol A ¹ has the meaning defined in structural formula (I) and the symbol B * represents a radical of general formula -CH2-CO- R ²⁷ , where the symbol R ²⁷ has the meaning defined in the structural formula (B10) [= compound (lB)] Scheme with et, Ν-dimethylformamide dimethylacetal to obtain the compound of structural formula (lC) (see diagram) and to react, with ring closure, the compound (lC) with hydroxylamine, or its salts, to get the compound from 10 structural formula (I-B10), where R ²⁸ = H or the compound (lB) is reacted with a compound of general formula (X1) HO-N = C (CI) -R ²⁸ (X1) where the symbol R ²⁸ has the meaning defined in the structural formula 15 (B10), with ring closure, to obtain the compound of structural formula (I-B10), in which the symbol R ²⁸ , in the general formula (X1), has a meaning such as 25/27 defined in the compound of structural formula (I-B10) to be prepared, with the exception of R ²⁸ = H, or (g) to prepare the compounds of structural formula (I), and their salts, in which symbol L represents a radical of structural formula -C (= A ¹ ) -B ¹ and symbol B ¹ represents a group of general formula (B10) [= compound (I-B10)], if a compound of formula is reacted structural (II) in which the symbols A ¹ , (R ¹ ) m and (R ² ) do not have the meanings defined in structural formula (I) and the symbol Y represents a leaving group, with a compound of structural formula X- (B10 ), where (B10) has a meaning as defined in group B ¹ and the symbol X represents a leaving group, optionally in the presence of a coupling agent, to obtain the compound of formula (I) (reaction of inter coupling) or reacting with an activated compound of structural formula X '- (B10), where the symbol X' represents a metal or derivative of metal, to obtain the compound of structural formula (I), (h) to prepare the compounds of structural formula (I), and their salts, in which L represents a radical of structural formula -C (= A ² ) -B ² and the symbol B ² represents a radical of general formula OR ³³ or SR ³⁴ , a compound of structural formula (I ') (R ² ) n (I') is reacted 26/27 where the symbols (R ¹ ) m and (R ² ) do not have the meanings defined in the structural formula (I), the symbol A ¹ represents an O or S radical and the symbol B ¹ represents a radical of structural formula ( B1), (B2), (B3), (B4), (B5), (B6), (B7), (B8), (B9), (B11), (B12), (B13) or (B14) , as defined above for compounds (I), where L represents a radical -C (= A ¹ ) -B ¹ , where each of symbols Q ¹ to Q ⁹ , in radicals B ¹ , represents OH or OM, with a compound of the general formula Y'-B ² , in which the symbol B ² has a meaning as defined in the radical L and the symbol Y 'represents a leaving group, to obtain the compound (I), in that the symbol B ² represents the radical OR ³³ , if A ¹ = O, or SR ³⁴ , if A ¹ = S, where the group -C (= A ² ) - in the compound (I), in comparison with the group -CB ¹ in the compound (I '), represents the most stable tautomer or a structurally fixed tautomer in which the radical -C (= A ² ) corresponds tautomerically to the radical = C (-B ¹ ) -, or (i) to prepare the compounds of formula (I), and their salts, where L represents a radical of formula -C (= A ² ) -B ² and the symbol B ² represents a radical of the general formula -NR ^B R ^C , a compound of structural formula (I ') is reacted in which the symbols (R ¹ ) m and (R ² ) do not have the meanings defined in the formula structural (I), the symbol A ¹ represents a radical of general formula -NR ^B and the symbol B ¹ represents a radical of structural formula (B1), (B2), (B3), (B4), (B5), ( B6), (B7), (B8), (B9), (B11), (B12), (B13) or (B14), as defined above for compounds (I), where L represents a radical -C (= A ¹ ) -B ¹ , where each of the symbols Q ¹ to Q ⁹ , in the radicals B ¹ , represents OH or OM, with a compound of the general formula Y'-R ^C , where the symbol R ^C has a meaning as defined in the radical -NR ^B R ^C of group B ² and the symbol Y ' 27/27 represents a leaving group, to obtain compound (I), in which the symbol B ² represents the radical -NR ^B R ^C , in which the group -C (= A ² ) - in the compound (I), compared to the -CB ¹ group in the compound (I '), it represents the most stable tautomer or a structurally fixed tautomer in which the radical -C (= A ² ) corresponds tautomerically to the radical = C (-B ¹ ) -. 13. Herbicidal or plant growth regulating composition, characterized by comprising one or more compounds of structural formula (I), or their salts, according to any one of claims 1 to 11, and usual formulation aids for crop protection agricultural 14. Method for controlling harmful plants or for regulating plant growth, characterized in that an effective amount of one or more compounds of structural formula (I), or their salts, according to any one of claims 1 to 11, is applied to plants, plant seeds, the soil on which or on which the plants grow or the area under cultivation. Method according to claim 14, characterized in that the compounds of formula (I), or their salts, are used to selectively control harmful plants or to regulate growth in crops of useful plants or ornamental plants. 16. Method according to claim 15, characterized in that the crop plants are transgenic crop plants. 17. Use of the compounds of structural formula (I), or their salts, according to any one of claims 1 to 11, characterized in that they are herbicides or plant growth regulators. Use according to claim 17, characterized in that the compounds are applied, as selective herbicides for the control of harmful plants or as regulators of plant growth, in useful or ornamental plant cultures.